Chromium(0)-promoted multicomponent cycloaddition of tethered diynes with cyclic trienes: Application to the total synthesis of 9-epi-pentalenic acid

Journal of Organic Chemistry

Volumn 69, Issue 20, 2004, Pages 6751-6760

  Rigby, James H ^a   Laxmisha, Mundruppady S ^a   Hudson, Andrew R ^a   Heap, Charles H ^a   Heeg, Mary Jane ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; HYDROLYSIS; ORGANIC ACIDS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

CYCLOADDITION; HYDROGENOLYSIS; REGIOSELECTIVITY; STEREOGENIC CENTERS;

CHROMIUM COMPOUNDS;

9 EPI PENTALENIC ACID; CHROMIUM; CYCLOPROPANE; PENTALENOLACTONE; UNCLASSIFIED DRUG;

ARTICLE; BAEYER VILLIGER REACTION; CYCLOADDITION; DRUG SYNTHESIS; HYDROGENOLYSIS; LACTONIZATION;

CHROMIUM; MODELS, CHEMICAL; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; SESQUITERPENES;

EID: 4644234796     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo040204o     Document Type: Article

References (95)

1. For general reviews on metal-catalyzed cycloadditions, see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92. (b) Hegedus, L. S. Coord. Chem. Rev. 1997, 161, 129-255. (c) Frühauf, H.-W. Chem. Rev. 1997, 97, 523-596. (d) Filippini, M-H.; Rodriguez, J. Chem. Rev. 1999, 99, 27-76. (e) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1998, 96, 635-662. (f) Hartley, R. C.; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477-501. (g) Wender, P. A. Pure Appl. Chem. 2002, 74, 25-31.
2. For general reviews on metal-catalyzed cycloadditions, see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92. (b) Hegedus, L. S. Coord. Chem. Rev. 1997, 161, 129-255. (c) Frühauf, H.-W. Chem. Rev. 1997, 97, 523-596. (d) Filippini, M-H.; Rodriguez, J. Chem. Rev. 1999, 99, 27-76. (e) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1998, 96, 635-662. (f) Hartley, R. C.; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477-501. (g) Wender, P. A. Pure Appl. Chem. 2002, 74, 25-31.
3. For general reviews on metal-catalyzed cycloadditions, see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92. (b) Hegedus, L. S. Coord. Chem. Rev. 1997, 161, 129-255. (c) Frühauf, H.-W. Chem. Rev. 1997, 97, 523-596. (d) Filippini, M-H.; Rodriguez, J. Chem. Rev. 1999, 99, 27-76. (e) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1998, 96, 635-662. (f) Hartley, R. C.; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477-501. (g) Wender, P. A. Pure Appl. Chem. 2002, 74, 25-31.
4. For general reviews on metal-catalyzed cycloadditions, see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92. (b) Hegedus, L. S. Coord. Chem. Rev. 1997, 161, 129-255. (c) Frühauf, H.-W. Chem. Rev. 1997, 97, 523-596. (d) Filippini, M-H.; Rodriguez, J. Chem. Rev. 1999, 99, 27-76. (e) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1998, 96, 635-662. (f) Hartley, R. C.; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477-501. (g) Wender, P. A. Pure Appl. Chem. 2002, 74, 25-31.
5. For general reviews on metal-catalyzed cycloadditions, see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92. (b) Hegedus, L. S. Coord. Chem. Rev. 1997, 161, 129-255. (c) Frühauf, H.-W. Chem. Rev. 1997, 97, 523-596. (d) Filippini, M-H.; Rodriguez, J. Chem. Rev. 1999, 99, 27-76. (e) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1998, 96, 635-662. (f) Hartley, R. C.; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477-501. (g) Wender, P. A. Pure Appl. Chem. 2002, 74, 25-31.
6. For general reviews on metal-catalyzed cycloadditions, see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92. (b) Hegedus, L. S. Coord. Chem. Rev. 1997, 161, 129-255. (c) Frühauf, H.-W. Chem. Rev. 1997, 97, 523-596. (d) Filippini, M-H.; Rodriguez, J. Chem. Rev. 1999, 99, 27-76. (e) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1998, 96, 635-662. (f) Hartley, R. C.; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477-501. (g) Wender, P. A. Pure Appl. Chem. 2002, 74, 25-31.
7. For general reviews on metal-catalyzed cycloadditions, see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92. (b) Hegedus, L. S. Coord. Chem. Rev. 1997, 161, 129-255. (c) Frühauf, H.-W. Chem. Rev. 1997, 97, 523-596. (d) Filippini, M-H.; Rodriguez, J. Chem. Rev. 1999, 99, 27-76. (e) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1998, 96, 635-662. (f) Hartley, R. C.; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477-501. (g) Wender, P. A. Pure Appl. Chem. 2002, 74, 25-31.
8. For general reviews on metal-promoted medium-size-ring synthesis, see: (a) Yet, L. Chem. Rev. 2000, 100, 2963-3008, (b) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (c) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Seven-membered-ring synthesis: (d) Trost, B. M.; Shen, H. C.; Schulz, T.; Koradin, C.; Schirok, H. Org. Lett. 2003, 5, 4149-4151. (e) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1993, 117, 4720-4721. (f) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154-15155. (g) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc, 1987, 109, 3483-3484. (h) Noyori, R. Acc. Chem. Res. 1979, 12, 61-66. (i) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1-19. (j) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275-8276. Eight-membered-ring synthesis: (k) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc. 2002, 124, 8782-8783. (l) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (m) Wender, P. A.; Correa, A. G.; Sato, Y.; Sun, R. J. Am. Chem. Soc. 2000, 122, 7815-7816. (n) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876-2877. (o) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784-8785. (p) Brenner, W.; Heimbach, P.; Hey, H.; Müller, E. W.; Wilke, G. Justus Liebigs Ann. Chem. 1869, 727, 161. (q) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913-1919. (r) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562-7564. (s) Lautens, M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513-4515. (t) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495-5506. Nine-membered ring: (u) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Scheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3-12. (v) Kreiter, C. G.; Lehr, K. J. Organomet. Chem. 1993, 454, 199-204. Ten-membered ring: (w) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382-1396.
9. For general reviews on metal-promoted medium-size-ring synthesis, see: (a) Yet, L. Chem. Rev. 2000, 100, 2963-3008, (b) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (c) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Seven-membered-ring synthesis: (d) Trost, B. M.; Shen, H. C.; Schulz, T.; Koradin, C.; Schirok, H. Org. Lett. 2003, 5, 4149-4151. (e) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1993, 117, 4720-4721. (f) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154-15155. (g) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc, 1987, 109, 3483-3484. (h) Noyori, R. Acc. Chem. Res. 1979, 12, 61-66. (i) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1-19. (j) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275-8276. Eight-membered-ring synthesis: (k) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc. 2002, 124, 8782-8783. (l) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (m) Wender, P. A.; Correa, A. G.; Sato, Y.; Sun, R. J. Am. Chem. Soc. 2000, 122, 7815-7816. (n) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876-2877. (o) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784-8785. (p) Brenner, W.; Heimbach, P.; Hey, H.; Müller, E. W.; Wilke, G. Justus Liebigs Ann. Chem. 1869, 727, 161. (q) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913-1919. (r) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562-7564. (s) Lautens, M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513-4515. (t) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495-5506. Nine-membered ring: (u) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Scheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3-12. (v) Kreiter, C. G.; Lehr, K. J. Organomet. Chem. 1993, 454, 199-204. Ten-membered ring: (w) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382-1396.
10. For general reviews on metal-promoted medium-size-ring synthesis, see: (a) Yet, L. Chem. Rev. 2000, 100, 2963-3008, (b) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (c) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Seven-membered-ring synthesis: (d) Trost, B. M.; Shen, H. C.; Schulz, T.; Koradin, C.; Schirok, H. Org. Lett. 2003, 5, 4149-4151. (e) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1993, 117, 4720-4721. (f) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154-15155. (g) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc, 1987, 109, 3483-3484. (h) Noyori, R. Acc. Chem. Res. 1979, 12, 61-66. (i) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1-19. (j) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275-8276. Eight-membered-ring synthesis: (k) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc. 2002, 124, 8782-8783. (l) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (m) Wender, P. A.; Correa, A. G.; Sato, Y.; Sun, R. J. Am. Chem. Soc. 2000, 122, 7815-7816. (n) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876-2877. (o) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784-8785. (p) Brenner, W.; Heimbach, P.; Hey, H.; Müller, E. W.; Wilke, G. Justus Liebigs Ann. Chem. 1869, 727, 161. (q) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913-1919. (r) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562-7564. (s) Lautens, M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513-4515. (t) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495-5506. Nine-membered ring: (u) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Scheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3-12. (v) Kreiter, C. G.; Lehr, K. J. Organomet. Chem. 1993, 454, 199-204. Ten-membered ring: (w) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382-1396.
11. For general reviews on metal-promoted medium-size-ring synthesis, see: (a) Yet, L. Chem. Rev. 2000, 100, 2963-3008, (b) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (c) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Seven-membered-ring synthesis: (d) Trost, B. M.; Shen, H. C.; Schulz, T.; Koradin, C.; Schirok, H. Org. Lett. 2003, 5, 4149-4151. (e) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1993, 117, 4720-4721. (f) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154-15155. (g) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc, 1987, 109, 3483-3484. (h) Noyori, R. Acc. Chem. Res. 1979, 12, 61-66. (i) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1-19. (j) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275-8276. Eight-membered-ring synthesis: (k) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc. 2002, 124, 8782-8783. (l) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (m) Wender, P. A.; Correa, A. G.; Sato, Y.; Sun, R. J. Am. Chem. Soc. 2000, 122, 7815-7816. (n) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876-2877. (o) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784-8785. (p) Brenner, W.; Heimbach, P.; Hey, H.; Müller, E. W.; Wilke, G. Justus Liebigs Ann. Chem. 1869, 727, 161. (q) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913-1919. (r) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562-7564. (s) Lautens, M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513-4515. (t) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495-5506. Nine-membered ring: (u) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Scheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3-12. (v) Kreiter, C. G.; Lehr, K. J. Organomet. Chem. 1993, 454, 199-204. Ten-membered ring: (w) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382-1396.
12. For general reviews on metal-promoted medium-size-ring synthesis, see: (a) Yet, L. Chem. Rev. 2000, 100, 2963-3008, (b) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (c) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Seven-membered-ring synthesis: (d) Trost, B. M.; Shen, H. C.; Schulz, T.; Koradin, C.; Schirok, H. Org. Lett. 2003, 5, 4149-4151. (e) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1993, 117, 4720-4721. (f) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154-15155. (g) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc, 1987, 109, 3483-3484. (h) Noyori, R. Acc. Chem. Res. 1979, 12, 61-66. (i) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1-19. (j) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275-8276. Eight-membered-ring synthesis: (k) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc. 2002, 124, 8782-8783. (l) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (m) Wender, P. A.; Correa, A. G.; Sato, Y.; Sun, R. J. Am. Chem. Soc. 2000, 122, 7815-7816. (n) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876-2877. (o) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784-8785. (p) Brenner, W.; Heimbach, P.; Hey, H.; Müller, E. W.; Wilke, G. Justus Liebigs Ann. Chem. 1869, 727, 161. (q) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913-1919. (r) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562-7564. (s) Lautens, M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513-4515. (t) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495-5506. Nine-membered ring: (u) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Scheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3-12. (v) Kreiter, C. G.; Lehr, K. J. Organomet. Chem. 1993, 454, 199-204. Ten-membered ring: (w) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382-1396.
13. For general reviews on metal-promoted medium-size-ring synthesis, see: (a) Yet, L. Chem. Rev. 2000, 100, 2963-3008, (b) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (c) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Seven-membered-ring synthesis: (d) Trost, B. M.; Shen, H. C.; Schulz, T.; Koradin, C.; Schirok, H. Org. Lett. 2003, 5, 4149-4151. (e) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1993, 117, 4720-4721. (f) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154-15155. (g) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc, 1987, 109, 3483-3484. (h) Noyori, R. Acc. Chem. Res. 1979, 12, 61-66. (i) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1-19. (j) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275-8276. Eight-membered-ring synthesis: (k) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc. 2002, 124, 8782-8783. (l) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (m) Wender, P. A.; Correa, A. G.; Sato, Y.; Sun, R. J. Am. Chem. Soc. 2000, 122, 7815-7816. (n) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876-2877. (o) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784-8785. (p) Brenner, W.; Heimbach, P.; Hey, H.; Müller, E. W.; Wilke, G. Justus Liebigs Ann. Chem. 1869, 727, 161. (q) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913-1919. (r) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562-7564. (s) Lautens, M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513-4515. (t) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495-5506. Nine-membered ring: (u) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Scheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3-12. (v) Kreiter, C. G.; Lehr, K. J. Organomet. Chem. 1993, 454, 199-204. Ten-membered ring: (w) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382-1396.
14. For general reviews on metal-promoted medium-size-ring synthesis, see: (a) Yet, L. Chem. Rev. 2000, 100, 2963-3008, (b) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (c) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Seven-membered-ring synthesis: (d) Trost, B. M.; Shen, H. C.; Schulz, T.; Koradin, C.; Schirok, H. Org. Lett. 2003, 5, 4149-4151. (e) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1993, 117, 4720-4721. (f) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154-15155. (g) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc, 1987, 109, 3483-3484. (h) Noyori, R. Acc. Chem. Res. 1979, 12, 61-66. (i) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1-19. (j) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275-8276. Eight-membered-ring synthesis: (k) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc. 2002, 124, 8782-8783. (l) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (m) Wender, P. A.; Correa, A. G.; Sato, Y.; Sun, R. J. Am. Chem. Soc. 2000, 122, 7815-7816. (n) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876-2877. (o) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784-8785. (p) Brenner, W.; Heimbach, P.; Hey, H.; Müller, E. W.; Wilke, G. Justus Liebigs Ann. Chem. 1869, 727, 161. (q) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913-1919. (r) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562-7564. (s) Lautens, M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513-4515. (t) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495-5506. Nine-membered ring: (u) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Scheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3-12. (v) Kreiter, C. G.; Lehr, K. J. Organomet. Chem. 1993, 454, 199-204. Ten-membered ring: (w) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382-1396.
15. For general reviews on metal-promoted medium-size-ring synthesis, see: (a) Yet, L. Chem. Rev. 2000, 100, 2963-3008, (b) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (c) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Seven-membered-ring synthesis: (d) Trost, B. M.; Shen, H. C.; Schulz, T.; Koradin, C.; Schirok, H. Org. Lett. 2003, 5, 4149-4151. (e) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1993, 117, 4720-4721. (f) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154-15155. (g) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc, 1987, 109, 3483-3484. (h) Noyori, R. Acc. Chem. Res. 1979, 12, 61-66. (i) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1-19. (j) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275-8276. Eight-membered-ring synthesis: (k) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc. 2002, 124, 8782-8783. (l) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (m) Wender, P. A.; Correa, A. G.; Sato, Y.; Sun, R. J. Am. Chem. Soc. 2000, 122, 7815-7816. (n) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876-2877. (o) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784-8785. (p) Brenner, W.; Heimbach, P.; Hey, H.; Müller, E. W.; Wilke, G. Justus Liebigs Ann. Chem. 1869, 727, 161. (q) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913-1919. (r) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562-7564. (s) Lautens, M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513-4515. (t) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495-5506. Nine-membered ring: (u) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Scheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3-12. (v) Kreiter, C. G.; Lehr, K. J. Organomet. Chem. 1993, 454, 199-204. Ten-membered ring: (w) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382-1396.
16. For general reviews on metal-promoted medium-size-ring synthesis, see: (a) Yet, L. Chem. Rev. 2000, 100, 2963-3008, (b) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (c) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Seven-membered-ring synthesis: (d) Trost, B. M.; Shen, H. C.; Schulz, T.; Koradin, C.; Schirok, H. Org. Lett. 2003, 5, 4149-4151. (e) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1993, 117, 4720-4721. (f) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154-15155. (g) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc, 1987, 109, 3483-3484. (h) Noyori, R. Acc. Chem. Res. 1979, 12, 61-66. (i) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1-19. (j) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275-8276. Eight-membered-ring synthesis: (k) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc. 2002, 124, 8782-8783. (l) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (m) Wender, P. A.; Correa, A. G.; Sato, Y.; Sun, R. J. Am. Chem. Soc. 2000, 122, 7815-7816. (n) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876-2877. (o) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784-8785. (p) Brenner, W.; Heimbach, P.; Hey, H.; Müller, E. W.; Wilke, G. Justus Liebigs Ann. Chem. 1869, 727, 161. (q) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913-1919. (r) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562-7564. (s) Lautens, M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513-4515. (t) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495-5506. Nine-membered ring: (u) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Scheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3-12. (v) Kreiter, C. G.; Lehr, K. J. Organomet. Chem. 1993, 454, 199-204. Ten-membered ring: (w) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382-1396.
17. For general reviews on metal-promoted medium-size-ring synthesis, see: (a) Yet, L. Chem. Rev. 2000, 100, 2963-3008, (b) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (c) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Seven-membered-ring synthesis: (d) Trost, B. M.; Shen, H. C.; Schulz, T.; Koradin, C.; Schirok, H. Org. Lett. 2003, 5, 4149-4151. (e) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1993, 117, 4720-4721. (f) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154-15155. (g) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc, 1987, 109, 3483-3484. (h) Noyori, R. Acc. Chem. Res. 1979, 12, 61-66. (i) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1-19. (j) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275-8276. Eight-membered-ring synthesis: (k) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc. 2002, 124, 8782-8783. (l) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (m) Wender, P. A.; Correa, A. G.; Sato, Y.; Sun, R. J. Am. Chem. Soc. 2000, 122, 7815-7816. (n) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876-2877. (o) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784-8785. (p) Brenner, W.; Heimbach, P.; Hey, H.; Müller, E. W.; Wilke, G. Justus Liebigs Ann. Chem. 1869, 727, 161. (q) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913-1919. (r) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562-7564. (s) Lautens, M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513-4515. (t) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495-5506. Nine-membered ring: (u) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Scheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3-12. (v) Kreiter, C. G.; Lehr, K. J. Organomet. Chem. 1993, 454, 199-204. Ten-membered ring: (w) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382-1396.
18. For general reviews on metal-promoted medium-size-ring synthesis, see: (a) Yet, L. Chem. Rev. 2000, 100, 2963-3008, (b) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (c) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Seven-membered-ring synthesis: (d) Trost, B. M.; Shen, H. C.; Schulz, T.; Koradin, C.; Schirok, H. Org. Lett. 2003, 5, 4149-4151. (e) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1993, 117, 4720-4721. (f) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154-15155. (g) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc, 1987, 109, 3483-3484. (h) Noyori, R. Acc. Chem. Res. 1979, 12, 61-66. (i) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1-19. (j) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275-8276. Eight-membered-ring synthesis: (k) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc. 2002, 124, 8782-8783. (l) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (m) Wender, P. A.; Correa, A. G.; Sato, Y.; Sun, R. J. Am. Chem. Soc. 2000, 122, 7815-7816. (n) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876-2877. (o) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784-8785. (p) Brenner, W.; Heimbach, P.; Hey, H.; Müller, E. W.; Wilke, G. Justus Liebigs Ann. Chem. 1869, 727, 161. (q) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913-1919. (r) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562-7564. (s) Lautens, M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513-4515. (t) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495-5506. Nine-membered ring: (u) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Scheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3-12. (v) Kreiter, C. G.; Lehr, K. J. Organomet. Chem. 1993, 454, 199-204. Ten-membered ring: (w) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382-1396.
19. For general reviews on metal-promoted medium-size-ring synthesis, see: (a) Yet, L. Chem. Rev. 2000, 100, 2963-3008, (b) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (c) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Seven-membered-ring synthesis: (d) Trost, B. M.; Shen, H. C.; Schulz, T.; Koradin, C.; Schirok, H. Org. Lett. 2003, 5, 4149-4151. (e) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1993, 117, 4720-4721. (f) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154-15155. (g) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc, 1987, 109, 3483-3484. (h) Noyori, R. Acc. Chem. Res. 1979, 12, 61-66. (i) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1-19. (j) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275-8276. Eight-membered-ring synthesis: (k) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc. 2002, 124, 8782-8783. (l) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (m) Wender, P. A.; Correa, A. G.; Sato, Y.; Sun, R. J. Am. Chem. Soc. 2000, 122, 7815-7816. (n) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876-2877. (o) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784-8785. (p) Brenner, W.; Heimbach, P.; Hey, H.; Müller, E. W.; Wilke, G. Justus Liebigs Ann. Chem. 1869, 727, 161. (q) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913-1919. (r) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562-7564. (s) Lautens, M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513-4515. (t) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495-5506. Nine-membered ring: (u) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Scheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3-12. (v) Kreiter, C. G.; Lehr, K. J. Organomet. Chem. 1993, 454, 199-204. Ten-membered ring: (w) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382-1396.
20. For general reviews on metal-promoted medium-size-ring synthesis, see: (a) Yet, L. Chem. Rev. 2000, 100, 2963-3008, (b) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (c) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Seven-membered-ring synthesis: (d) Trost, B. M.; Shen, H. C.; Schulz, T.; Koradin, C.; Schirok, H. Org. Lett. 2003, 5, 4149-4151. (e) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1993, 117, 4720-4721. (f) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154-15155. (g) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc, 1987, 109, 3483-3484. (h) Noyori, R. Acc. Chem. Res. 1979, 12, 61-66. (i) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1-19. (j) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275-8276. Eight-membered-ring synthesis: (k) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc. 2002, 124, 8782-8783. (l) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (m) Wender, P. A.; Correa, A. G.; Sato, Y.; Sun, R. J. Am. Chem. Soc. 2000, 122, 7815-7816. (n) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876-2877. (o) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784-8785. (p) Brenner, W.; Heimbach, P.; Hey, H.; Müller, E. W.; Wilke, G. Justus Liebigs Ann. Chem. 1869, 727, 161. (q) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913-1919. (r) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562-7564. (s) Lautens, M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513-4515. (t) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495-5506. Nine-membered ring: (u) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Scheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3-12. (v) Kreiter, C. G.; Lehr, K. J. Organomet. Chem. 1993, 454, 199-204. Ten-membered ring: (w) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382-1396.
21. For general reviews on metal-promoted medium-size-ring synthesis, see: (a) Yet, L. Chem. Rev. 2000, 100, 2963-3008, (b) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (c) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Seven-membered-ring synthesis: (d) Trost, B. M.; Shen, H. C.; Schulz, T.; Koradin, C.; Schirok, H. Org. Lett. 2003, 5, 4149-4151. (e) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1993, 117, 4720-4721. (f) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154-15155. (g) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc, 1987, 109, 3483-3484. (h) Noyori, R. Acc. Chem. Res. 1979, 12, 61-66. (i) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1-19. (j) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275-8276. Eight-membered-ring synthesis: (k) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc. 2002, 124, 8782-8783. (l) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (m) Wender, P. A.; Correa, A. G.; Sato, Y.; Sun, R. J. Am. Chem. Soc. 2000, 122, 7815-7816. (n) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876-2877. (o) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784-8785. (p) Brenner, W.; Heimbach, P.; Hey, H.; Müller, E. W.; Wilke, G. Justus Liebigs Ann. Chem. 1869, 727, 161. (q) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913-1919. (r) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562-7564. (s) Lautens, M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513-4515. (t) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495-5506. Nine-membered ring: (u) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Scheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3-12. (v) Kreiter, C. G.; Lehr, K. J. Organomet. Chem. 1993, 454, 199-204. Ten-membered ring: (w) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382-1396.
22. For general reviews on metal-promoted medium-size-ring synthesis, see: (a) Yet, L. Chem. Rev. 2000, 100, 2963-3008, (b) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (c) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Seven-membered-ring synthesis: (d) Trost, B. M.; Shen, H. C.; Schulz, T.; Koradin, C.; Schirok, H. Org. Lett. 2003, 5, 4149-4151. (e) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1993, 117, 4720-4721. (f) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154-15155. (g) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc, 1987, 109, 3483-3484. (h) Noyori, R. Acc. Chem. Res. 1979, 12, 61-66. (i) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1-19. (j) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275-8276. Eight-membered-ring synthesis: (k) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc. 2002, 124, 8782-8783. (l) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (m) Wender, P. A.; Correa, A. G.; Sato, Y.; Sun, R. J. Am. Chem. Soc. 2000, 122, 7815-7816. (n) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876-2877. (o) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784-8785. (p) Brenner, W.; Heimbach, P.; Hey, H.; Müller, E. W.; Wilke, G. Justus Liebigs Ann. Chem. 1869, 727, 161. (q) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913-1919. (r) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562-7564. (s) Lautens, M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513-4515. (t) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495-5506. Nine-membered ring: (u) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Scheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3-12. (v) Kreiter, C. G.; Lehr, K. J. Organomet. Chem. 1993, 454, 199-204. Ten-membered ring: (w) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382-1396.
23. For general reviews on metal-promoted medium-size-ring synthesis, see: (a) Yet, L. Chem. Rev. 2000, 100, 2963-3008, (b) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (c) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Seven-membered-ring synthesis: (d) Trost, B. M.; Shen, H. C.; Schulz, T.; Koradin, C.; Schirok, H. Org. Lett. 2003, 5, 4149-4151. (e) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1993, 117, 4720-4721. (f) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154-15155. (g) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc, 1987, 109, 3483-3484. (h) Noyori, R. Acc. Chem. Res. 1979, 12, 61-66. (i) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1-19. (j) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275-8276. Eight-membered-ring synthesis: (k) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc. 2002, 124, 8782-8783. (l) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (m) Wender, P. A.; Correa, A. G.; Sato, Y.; Sun, R. J. Am. Chem. Soc. 2000, 122, 7815-7816. (n) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876-2877. (o) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784-8785. (p) Brenner, W.; Heimbach, P.; Hey, H.; Müller, E. W.; Wilke, G. Justus Liebigs Ann. Chem. 1869, 727, 161. (q) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913-1919. (r) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562-7564. (s) Lautens, M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513-4515. (t) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495-5506. Nine-membered ring: (u) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Scheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3-12. (v) Kreiter, C. G.; Lehr, K. J. Organomet. Chem. 1993, 454, 199-204. Ten-membered ring: (w) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382-1396.
24. For general reviews on metal-promoted medium-size-ring synthesis, see: (a) Yet, L. Chem. Rev. 2000, 100, 2963-3008, (b) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (c) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Seven-membered-ring synthesis: (d) Trost, B. M.; Shen, H. C.; Schulz, T.; Koradin, C.; Schirok, H. Org. Lett. 2003, 5, 4149-4151. (e) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1993, 117, 4720-4721. (f) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154-15155. (g) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc, 1987, 109, 3483-3484. (h) Noyori, R. Acc. Chem. Res. 1979, 12, 61-66. (i) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1-19. (j) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275-8276. Eight-membered-ring synthesis: (k) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc. 2002, 124, 8782-8783. (l) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (m) Wender, P. A.; Correa, A. G.; Sato, Y.; Sun, R. J. Am. Chem. Soc. 2000, 122, 7815-7816. (n) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876-2877. (o) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784-8785. (p) Brenner, W.; Heimbach, P.; Hey, H.; Müller, E. W.; Wilke, G. Justus Liebigs Ann. Chem. 1869, 727, 161. (q) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913-1919. (r) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562-7564. (s) Lautens, M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513-4515. (t) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495-5506. Nine-membered ring: (u) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Scheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3-12. (v) Kreiter, C. G.; Lehr, K. J. Organomet. Chem. 1993, 454, 199-204. Ten-membered ring: (w) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382-1396.
25. For general reviews on metal-promoted medium-size-ring synthesis, see: (a) Yet, L. Chem. Rev. 2000, 100, 2963-3008, (b) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (c) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Seven-membered-ring synthesis: (d) Trost, B. M.; Shen, H. C.; Schulz, T.; Koradin, C.; Schirok, H. Org. Lett. 2003, 5, 4149-4151. (e) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1993, 117, 4720-4721. (f) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154-15155. (g) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc, 1987, 109, 3483-3484. (h) Noyori, R. Acc. Chem. Res. 1979, 12, 61-66. (i) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1-19. (j) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275-8276. Eight-membered-ring synthesis: (k) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc. 2002, 124, 8782-8783. (l) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (m) Wender, P. A.; Correa, A. G.; Sato, Y.; Sun, R. J. Am. Chem. Soc. 2000, 122, 7815-7816. (n) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876-2877. (o) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784-8785. (p) Brenner, W.; Heimbach, P.; Hey, H.; Müller, E. W.; Wilke, G. Justus Liebigs Ann. Chem. 1869, 727, 161. (q) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913-1919. (r) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562-7564. (s) Lautens, M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513-4515. (t) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495-5506. Nine-membered ring: (u) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Scheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3-12. (v) Kreiter, C. G.; Lehr, K. J. Organomet. Chem. 1993, 454, 199-204. Ten-membered ring: (w) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382-1396.
26. For general reviews on metal-promoted medium-size-ring synthesis, see: (a) Yet, L. Chem. Rev. 2000, 100, 2963-3008, (b) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (c) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Seven-membered-ring synthesis: (d) Trost, B. M.; Shen, H. C.; Schulz, T.; Koradin, C.; Schirok, H. Org. Lett. 2003, 5, 4149-4151. (e) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1993, 117, 4720-4721. (f) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154-15155. (g) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc, 1987, 109, 3483-3484. (h) Noyori, R. Acc. Chem. Res. 1979, 12, 61-66. (i) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1-19. (j) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275-8276. Eight-membered-ring synthesis: (k) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc. 2002, 124, 8782-8783. (l) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (m) Wender, P. A.; Correa, A. G.; Sato, Y.; Sun, R. J. Am. Chem. Soc. 2000, 122, 7815-7816. (n) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876-2877. (o) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784-8785. (p) Brenner, W.; Heimbach, P.; Hey, H.; Müller, E. W.; Wilke, G. Justus Liebigs Ann. Chem. 1869, 727, 161. (q) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913-1919. (r) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562-7564. (s) Lautens, M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513-4515. (t) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495-5506. Nine-membered ring: (u) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Scheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3-12. (v) Kreiter, C. G.; Lehr, K. J. Organomet. Chem. 1993, 454, 199-204. Ten-membered ring: (w) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382-1396.
27. For general reviews on metal-promoted medium-size-ring synthesis, see: (a) Yet, L. Chem. Rev. 2000, 100, 2963-3008, (b) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (c) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Seven-membered-ring synthesis: (d) Trost, B. M.; Shen, H. C.; Schulz, T.; Koradin, C.; Schirok, H. Org. Lett. 2003, 5, 4149-4151. (e) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1993, 117, 4720-4721. (f) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154-15155. (g) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc, 1987, 109, 3483-3484. (h) Noyori, R. Acc. Chem. Res. 1979, 12, 61-66. (i) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1-19. (j) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275-8276. Eight-membered-ring synthesis: (k) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc. 2002, 124, 8782-8783. (l) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (m) Wender, P. A.; Correa, A. G.; Sato, Y.; Sun, R. J. Am. Chem. Soc. 2000, 122, 7815-7816. (n) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876-2877. (o) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784-8785. (p) Brenner, W.; Heimbach, P.; Hey, H.; Müller, E. W.; Wilke, G. Justus Liebigs Ann. Chem. 1869, 727, 161. (q) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913-1919. (r) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562-7564. (s) Lautens, M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513-4515. (t) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495-5506. Nine-membered ring: (u) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Scheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3-12. (v) Kreiter, C. G.; Lehr, K. J. Organomet. Chem. 1993, 454, 199-204. Ten-membered ring: (w) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382-1396.
28. For general reviews on metal-promoted medium-size-ring synthesis, see: (a) Yet, L. Chem. Rev. 2000, 100, 2963-3008, (b) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (c) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Seven-membered-ring synthesis: (d) Trost, B. M.; Shen, H. C.; Schulz, T.; Koradin, C.; Schirok, H. Org. Lett. 2003, 5, 4149-4151. (e) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1993, 117, 4720-4721. (f) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154-15155. (g) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc, 1987, 109, 3483-3484. (h) Noyori, R. Acc. Chem. Res. 1979, 12, 61-66. (i) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1-19. (j) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275-8276. Eight-membered-ring synthesis: (k) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc. 2002, 124, 8782-8783. (l) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (m) Wender, P. A.; Correa, A. G.; Sato, Y.; Sun, R. J. Am. Chem. Soc. 2000, 122, 7815-7816. (n) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876-2877. (o) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784-8785. (p) Brenner, W.; Heimbach, P.; Hey, H.; Müller, E. W.; Wilke, G. Justus Liebigs Ann. Chem. 1869, 727, 161. (q) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913-1919. (r) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562-7564. (s) Lautens, M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513-4515. (t) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495-5506. Nine-membered ring: (u) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Scheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3-12. (v) Kreiter, C. G.; Lehr, K. J. Organomet. Chem. 1993, 454, 199-204. Ten-membered ring: (w) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382-1396.
29. For general reviews on metal-promoted medium-size-ring synthesis, see: (a) Yet, L. Chem. Rev. 2000, 100, 2963-3008, (b) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (c) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Seven-membered-ring synthesis: (d) Trost, B. M.; Shen, H. C.; Schulz, T.; Koradin, C.; Schirok, H. Org. Lett. 2003, 5, 4149-4151. (e) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1993, 117, 4720-4721. (f) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154-15155. (g) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc, 1987, 109, 3483-3484. (h) Noyori, R. Acc. Chem. Res. 1979, 12, 61-66. (i) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1-19. (j) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275-8276. Eight-membered-ring synthesis: (k) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc. 2002, 124, 8782-8783. (l) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (m) Wender, P. A.; Correa, A. G.; Sato, Y.; Sun, R. J. Am. Chem. Soc. 2000, 122, 7815-7816. (n) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876-2877. (o) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784-8785. (p) Brenner, W.; Heimbach, P.; Hey, H.; Müller, E. W.; Wilke, G. Justus Liebigs Ann. Chem. 1869, 727, 161. (q) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913-1919. (r) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562-7564. (s) Lautens, M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513-4515. (t) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495-5506. Nine-membered ring: (u) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Scheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3-12. (v) Kreiter, C. G.; Lehr, K. J. Organomet. Chem. 1993, 454, 199-204. Ten-membered ring: (w) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382-1396.
30. For general reviews on metal-promoted medium-size-ring synthesis, see: (a) Yet, L. Chem. Rev. 2000, 100, 2963-3008, (b) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (c) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282. Seven-membered-ring synthesis: (d) Trost, B. M.; Shen, H. C.; Schulz, T.; Koradin, C.; Schirok, H. Org. Lett. 2003, 5, 4149-4151. (e) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1993, 117, 4720-4721. (f) Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154-15155. (g) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc, 1987, 109, 3483-3484. (h) Noyori, R. Acc. Chem. Res. 1979, 12, 61-66. (i) Hoffmann, H. M. R. Angew Chem., Int. Ed. Engl. 1984, 23, 1-19. (j) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275-8276. Eight-membered-ring synthesis: (k) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc. 2002, 124, 8782-8783. (l) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (m) Wender, P. A.; Correa, A. G.; Sato, Y.; Sun, R. J. Am. Chem. Soc. 2000, 122, 7815-7816. (n) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876-2877. (o) Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784-8785. (p) Brenner, W.; Heimbach, P.; Hey, H.; Müller, E. W.; Wilke, G. Justus Liebigs Ann. Chem. 1869, 727, 161. (q) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913-1919. (r) Davis, R. E.; Dodds, T. A.; Hseu, T.-H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562-7564. (s) Lautens, M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513-4515. (t) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495-5506. Nine-membered ring: (u) Kreiter, C. G.; Lehr, K.; Leyendecker, M.; Scheldrick, W. S.; Exner, R. Chem. Ber. 1991, 124, 3-12. (v) Kreiter, C. G.; Lehr, K. J. Organomet. Chem. 1993, 454, 199-204. Ten-membered ring: (w) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382-1396.
31. (a) Rigby, J. H. Tetrahedron 1999, 55, 4521-4538.
32. (b) Rigby, J. H. Acc. Chem. Res. 1993, 26, 579-585.
33. (c) Chaffee, K.; Huo, P.; Sheridan, J. B.; Barbieri, A.; Aistars, A.; Lalancette, R. A.; Ostrander, R. L.; Rheingold, A. L. J. Am. Chem. Soc. 1995, 117, 1900-1907.
34. (d) Chaffee, K.; Sheridan, J. B.; Aistars, A. Organometallics 1992, 11, 18-19,
35. (e) Özkar, S.; Kurz, H.; Neugebauer, D.; Kreiter, C. G. J. Organomet. Chem. 1978, 160, 115-124.
36. (a) Rigby, J. H.; Warshakoon, N. C.; Heeg, M. J. J. Am. Chem. Soc. 1996, 118, 6094-6095.
37. (b) Chen, W.; Chaffee, K.; Chung, H.-J.; Sheridan, J. B. J. Am. Chem. Soc. 1996, 118, 9980-9981.
38. Rigby, J. H.; Heap, C. R.; Warshakoon, N. C. Tetrahedron 2000, 56, 2305-2311.
39. Seto, H.; Sasaki, T.; Uzawa, J.; Takeuchi, S.; Yonehara, H. Tetrahedron Lett. 1978, 19, 4411-4412.
40. For excellent reviews of approaches to triquinane ring systems and related natural products, see: (a) Mehta, G.; Srikrishna, A. Chem. Rev. 1997, 97, 671-720. (b) Paquette, L. A. Top. Curr. Chem. 1979, 79, 41-165. (c) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1-158. For previous syntheses of pentalenic acid, see: (d) Crimmins, M. T.; DeLoach, J. A. J. Am. Chem. Soc. 1986, 108, 800-806. (e) Crimmins, M. T.; DeLoach, J. A. J. Org. Chem. 1984, 49, 2076-2077. (f) Sakai, K.; Ohtsuka, T.; Misumi, S. Chem. Lett. 1981, 355-358. (g) Agnel, G.; Negishi, E. J. Am. Chem. Soc. 1991, 113, 7424-7426. (h) Ihara, M.; Katogi, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1988, 2963-2970. (i) Hudlicky, T.; Sinai-Zingde, G.; Natchus, M. G.; Ranu, B. C.; Papadopolous, P. Tetrahedron 1987, 43, 5685-5721. For previous approaches to pentalenic acid, see: (J) Bintz-Giudicelli, C.; Weymann, O.; Uguen, D. Tetrahedron Lett. 1997, 38, 2841-2844. (k) Rowley, E. G.; Schore, N. E. J. Org. Chem. 1992, 57, 6853-6861. (l) Seo, J.; Fain, H.; Blanc, J.-B.; Montgomery, J. J. Org. Chem. 1999, 64, 6060-6065.
41. For excellent reviews of approaches to triquinane ring systems and related natural products, see: (a) Mehta, G.; Srikrishna, A. Chem. Rev. 1997, 97, 671-720. (b) Paquette, L. A. Top. Curr. Chem. 1979, 79, 41-165. (c) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1-158. For previous syntheses of pentalenic acid, see: (d) Crimmins, M. T.; DeLoach, J. A. J. Am. Chem. Soc. 1986, 108, 800-806. (e) Crimmins, M. T.; DeLoach, J. A. J. Org. Chem. 1984, 49, 2076-2077. (f) Sakai, K.; Ohtsuka, T.; Misumi, S. Chem. Lett. 1981, 355-358. (g) Agnel, G.; Negishi, E. J. Am. Chem. Soc. 1991, 113, 7424-7426. (h) Ihara, M.; Katogi, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1988, 2963-2970. (i) Hudlicky, T.; Sinai-Zingde, G.; Natchus, M. G.; Ranu, B. C.; Papadopolous, P. Tetrahedron 1987, 43, 5685-5721. For previous approaches to pentalenic acid, see: (J) Bintz-Giudicelli, C.; Weymann, O.; Uguen, D. Tetrahedron Lett. 1997, 38, 2841-2844. (k) Rowley, E. G.; Schore, N. E. J. Org. Chem. 1992, 57, 6853-6861. (l) Seo, J.; Fain, H.; Blanc, J.-B.; Montgomery, J. J. Org. Chem. 1999, 64, 6060-6065.
42. For excellent reviews of approaches to triquinane ring systems and related natural products, see: (a) Mehta, G.; Srikrishna, A. Chem. Rev. 1997, 97, 671-720. (b) Paquette, L. A. Top. Curr. Chem. 1979, 79, 41-165. (c) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1-158. For previous syntheses of pentalenic acid, see: (d) Crimmins, M. T.; DeLoach, J. A. J. Am. Chem. Soc. 1986, 108, 800-806. (e) Crimmins, M. T.; DeLoach, J. A. J. Org. Chem. 1984, 49, 2076-2077. (f) Sakai, K.; Ohtsuka, T.; Misumi, S. Chem. Lett. 1981, 355-358. (g) Agnel, G.; Negishi, E. J. Am. Chem. Soc. 1991, 113, 7424-7426. (h) Ihara, M.; Katogi, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1988, 2963-2970. (i) Hudlicky, T.; Sinai-Zingde, G.; Natchus, M. G.; Ranu, B. C.; Papadopolous, P. Tetrahedron 1987, 43, 5685-5721. For previous approaches to pentalenic acid, see: (J) Bintz-Giudicelli, C.; Weymann, O.; Uguen, D. Tetrahedron Lett. 1997, 38, 2841-2844. (k) Rowley, E. G.; Schore, N. E. J. Org. Chem. 1992, 57, 6853-6861. (l) Seo, J.; Fain, H.; Blanc, J.-B.; Montgomery, J. J. Org. Chem. 1999, 64, 6060-6065.
43. For excellent reviews of approaches to triquinane ring systems and related natural products, see: (a) Mehta, G.; Srikrishna, A. Chem. Rev. 1997, 97, 671-720. (b) Paquette, L. A. Top. Curr. Chem. 1979, 79, 41-165. (c)
44. For excellent reviews of approaches to triquinane ring systems and related natural products, see: (a) Mehta, G.; Srikrishna, A. Chem. Rev. 1997, 97, 671-720. (b) Paquette, L. A. Top. Curr. Chem. 1979, 79, 41-165. (c) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1-158. For previous syntheses of pentalenic acid, see: (d) Crimmins, M. T.; DeLoach, J. A. J. Am. Chem. Soc. 1986, 108, 800-806. (e) Crimmins, M. T.; DeLoach, J. A. J. Org. Chem. 1984, 49, 2076-2077. (f) Sakai, K.; Ohtsuka, T.; Misumi, S. Chem. Lett. 1981, 355-358. (g) Agnel, G.; Negishi, E. J. Am. Chem. Soc. 1991, 113, 7424-7426. (h) Ihara, M.; Katogi, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1988, 2963-2970. (i) Hudlicky, T.; Sinai-Zingde, G.; Natchus, M. G.; Ranu, B. C.; Papadopolous, P. Tetrahedron 1987, 43, 5685-5721. For previous approaches to pentalenic acid, see: (J) Bintz-Giudicelli, C.; Weymann, O.; Uguen, D. Tetrahedron Lett. 1997, 38, 2841-2844. (k) Rowley, E. G.; Schore, N. E. J. Org. Chem. 1992, 57, 6853-6861. (l) Seo, J.; Fain, H.; Blanc, J.-B.; Montgomery, J. J. Org. Chem. 1999, 64, 6060-6065.
45. For excellent reviews of approaches to triquinane ring systems and related natural products, see: (a) Mehta, G.; Srikrishna, A. Chem. Rev. 1997, 97, 671-720. (b) Paquette, L. A. Top. Curr. Chem. 1979, 79, 41-165. (c) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1-158. For previous syntheses of pentalenic acid, see: (d) Crimmins, M. T.; DeLoach, J. A. J. Am. Chem. Soc. 1986, 108, 800-806. (e) Crimmins, M. T.; DeLoach, J. A. J. Org. Chem. 1984, 49, 2076-2077. (f) Sakai, K.; Ohtsuka, T.; Misumi, S. Chem. Lett. 1981, 355-358. (g) Agnel, G.; Negishi, E. J. Am. Chem. Soc. 1991, 113, 7424-7426. (h) Ihara, M.; Katogi, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1988, 2963-2970. (i) Hudlicky, T.; Sinai-Zingde, G.; Natchus, M. G.; Ranu, B. C.; Papadopolous, P. Tetrahedron 1987, 43, 5685-5721. For previous approaches to pentalenic acid, see: (J) Bintz-Giudicelli, C.; Weymann, O.; Uguen, D. Tetrahedron Lett. 1997, 38, 2841-2844. (k) Rowley, E. G.; Schore, N. E. J. Org. Chem. 1992, 57, 6853-6861. (l) Seo, J.; Fain, H.; Blanc, J.-B.; Montgomery, J. J. Org. Chem. 1999, 64, 6060-6065.
46. For excellent reviews of approaches to triquinane ring systems and related natural products, see: (a) Mehta, G.; Srikrishna, A. Chem. Rev. 1997, 97, 671-720. (b) Paquette, L. A. Top. Curr. Chem. 1979, 79, 41-165. (c) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1-158. For previous syntheses of pentalenic acid, see: (d) Crimmins, M. T.; DeLoach, J. A. J. Am. Chem. Soc. 1986, 108, 800-806. (e) Crimmins, M. T.; DeLoach, J. A. J. Org. Chem. 1984, 49, 2076-2077. (f) Sakai, K.; Ohtsuka, T.; Misumi, S. Chem. Lett. 1981, 355-358. (g) Agnel, G.; Negishi, E. J. Am. Chem. Soc. 1991, 113, 7424-7426. (h) Ihara, M.; Katogi, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1988, 2963-2970. (i) Hudlicky, T.; Sinai-Zingde, G.; Natchus, M. G.; Ranu, B. C.; Papadopolous, P. Tetrahedron 1987, 43, 5685-5721. For previous approaches to pentalenic acid, see: (J) Bintz-Giudicelli, C.; Weymann, O.; Uguen, D. Tetrahedron Lett. 1997, 38, 2841-2844. (k) Rowley, E. G.; Schore, N. E. J. Org. Chem. 1992, 57, 6853-6861. (l) Seo, J.; Fain, H.; Blanc, J.-B.; Montgomery, J. J. Org. Chem. 1999, 64, 6060-6065.
47. For excellent reviews of approaches to triquinane ring systems and related natural products, see: (a) Mehta, G.; Srikrishna, A. Chem. Rev. 1997, 97, 671-720. (b) Paquette, L. A. Top. Curr. Chem. 1979, 79, 41-165. (c) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1-158. For previous syntheses of pentalenic acid, see: (d) Crimmins, M. T.; DeLoach, J. A. J. Am. Chem. Soc. 1986, 108, 800-806. (e) Crimmins, M. T.; DeLoach, J. A. J. Org. Chem. 1984, 49, 2076-2077. (f) Sakai, K.; Ohtsuka, T.; Misumi, S. Chem. Lett. 1981, 355-358. (g) Agnel, G.; Negishi, E. J. Am. Chem. Soc. 1991, 113, 7424-7426. (h) Ihara, M.; Katogi, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1988, 2963-2970. (i) Hudlicky, T.; Sinai-Zingde, G.; Natchus, M. G.; Ranu, B. C.; Papadopolous, P. Tetrahedron 1987, 43, 5685-5721. For previous approaches to pentalenic acid, see: (J) Bintz-Giudicelli, C.; Weymann, O.; Uguen, D. Tetrahedron Lett. 1997, 38, 2841-2844. (k) Rowley, E. G.; Schore, N. E. J. Org. Chem. 1992, 57, 6853-6861. (l) Seo, J.; Fain, H.; Blanc, J.-B.; Montgomery, J. J. Org. Chem. 1999, 64, 6060-6065.
48. For excellent reviews of approaches to triquinane ring systems and related natural products, see: (a) Mehta, G.; Srikrishna, A. Chem. Rev. 1997, 97, 671-720. (b) Paquette, L. A. Top. Curr. Chem. 1979, 79, 41-165. (c) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1-158. For previous syntheses of pentalenic acid, see: (d) Crimmins, M. T.; DeLoach, J. A. J. Am. Chem. Soc. 1986, 108, 800-806. (e) Crimmins, M. T.; DeLoach, J. A. J. Org. Chem. 1984, 49, 2076-2077. (f) Sakai, K.; Ohtsuka, T.; Misumi, S. Chem. Lett. 1981, 355-358. (g) Agnel, G.; Negishi, E. J. Am. Chem. Soc. 1991, 113, 7424-7426. (h) Ihara, M.; Katogi, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1988, 2963-2970. (i) Hudlicky, T.; Sinai-Zingde, G.; Natchus, M. G.; Ranu, B. C.; Papadopolous, P. Tetrahedron 1987, 43, 5685-5721. For previous approaches to pentalenic acid, see: (J) Bintz-Giudicelli, C.; Weymann, O.; Uguen, D. Tetrahedron Lett. 1997, 38, 2841-2844. (k) Rowley, E. G.; Schore, N. E. J. Org. Chem. 1992, 57, 6853-6861. (l) Seo, J.; Fain, H.; Blanc, J.-B.; Montgomery, J. J. Org. Chem. 1999, 64, 6060-6065.
49. For excellent reviews of approaches to triquinane ring systems and related natural products, see: (a) Mehta, G.; Srikrishna, A. Chem. Rev. 1997, 97, 671-720. (b) Paquette, L. A. Top. Curr. Chem. 1979, 79, 41-165. (c) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1-158. For previous syntheses of pentalenic acid, see: (d) Crimmins, M. T.; DeLoach, J. A. J. Am. Chem. Soc. 1986, 108, 800-806. (e) Crimmins, M. T.; DeLoach, J. A. J. Org. Chem. 1984, 49, 2076-2077. (f) Sakai, K.; Ohtsuka, T.; Misumi, S. Chem. Lett. 1981, 355-358. (g) Agnel, G.; Negishi, E. J. Am. Chem. Soc. 1991, 113, 7424-7426. (h) Ihara, M.; Katogi, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1988, 2963-2970. (i) Hudlicky, T.; Sinai-Zingde, G.; Natchus, M. G.; Ranu, B. C.; Papadopolous, P. Tetrahedron 1987, 43, 5685-5721. For previous approaches to pentalenic acid, see: (J) Bintz-Giudicelli, C.; Weymann, O.; Uguen, D. Tetrahedron Lett. 1997, 38, 2841-2844. (k) Rowley, E. G.; Schore, N. E. J. Org. Chem. 1992, 57, 6853-6861. (l) Seo, J.; Fain, H.; Blanc, J.-B.; Montgomery, J. J. Org. Chem. 1999, 64, 6060-6065.
50. For excellent reviews of approaches to triquinane ring systems and related natural products, see: (a) Mehta, G.; Srikrishna, A. Chem. Rev. 1997, 97, 671-720. (b) Paquette, L. A. Top. Curr. Chem. 1979, 79, 41-165. (c) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1-158. For previous syntheses of pentalenic acid, see: (d) Crimmins, M. T.; DeLoach, J. A. J. Am. Chem. Soc. 1986, 108, 800-806. (e) Crimmins, M. T.; DeLoach, J. A. J. Org. Chem. 1984, 49, 2076-2077. (f) Sakai, K.; Ohtsuka, T.; Misumi, S. Chem. Lett. 1981, 355-358. (g) Agnel, G.; Negishi, E. J. Am. Chem. Soc. 1991, 113, 7424-7426. (h) Ihara, M.; Katogi, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1988, 2963-2970. (i) Hudlicky, T.; Sinai-Zingde, G.; Natchus, M. G.; Ranu, B. C.; Papadopolous, P. Tetrahedron 1987, 43, 5685-5721. For previous approaches to pentalenic acid, see: (J) Bintz-Giudicelli, C.; Weymann, O.; Uguen, D. Tetrahedron Lett. 1997, 38, 2841-2844. (k) Rowley, E. G.; Schore, N. E. J. Org. Chem. 1992, 57, 6853-6861. (l) Seo, J.; Fain, H.; Blanc, J.-B.; Montgomery, J. J. Org. Chem. 1999, 64, 6060-6065.
51. For excellent reviews of approaches to triquinane ring systems and related natural products, see: (a) Mehta, G.; Srikrishna, A. Chem. Rev. 1997, 97, 671-720. (b) Paquette, L. A. Top. Curr. Chem. 1979, 79, 41-165. (c) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1-158. For previous syntheses of pentalenic acid, see: (d) Crimmins, M. T.; DeLoach, J. A. J. Am. Chem. Soc. 1986, 108, 800-806. (e) Crimmins, M. T.; DeLoach, J. A. J. Org. Chem. 1984, 49, 2076-2077. (f) Sakai, K.; Ohtsuka, T.; Misumi, S. Chem. Lett. 1981, 355-358. (g) Agnel, G.; Negishi, E. J. Am. Chem. Soc. 1991, 113, 7424-7426. (h) Ihara, M.; Katogi, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1988, 2963-2970. (i) Hudlicky, T.; Sinai-Zingde, G.; Natchus, M. G.; Ranu, B. C.; Papadopolous, P. Tetrahedron 1987, 43, 5685-5721. For previous approaches to pentalenic acid, see: (J) Bintz-Giudicelli, C.; Weymann, O.; Uguen, D. Tetrahedron Lett. 1997, 38, 2841-2844. (k) Rowley, E. G.; Schore, N. E. J. Org. Chem. 1992, 57, 6853-6861. (l) Seo, J.; Fain, H.; Blanc, J.-B.; Montgomery, J. J. Org. Chem. 1999, 64, 6060-6065.
52. Trost, B. M. Science 1991, 254, 1471-1484.
53. (a) Magnus, P.; Principe, L. M.; Slater, M. J. J. Org. Chem. 1987, 52, 1483-1486.
54. (b) Ojima, I.; Kass, D. F.; Zhu, J. Organometallics 1996, 15, 5191-5195.
55. (c) Pearson, A. J.; Shively, Jr, R. J. Organometallics 1994, 13, 578-584.
56. (d) Yamamoto, Y.; Kitahara, H.; Ogawa, R.; Kawaguchi, H.; Tatsumi, K.; Itoh, K. J. Am. Chem. Soc. 2000, 122, 4310-4319.
57. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825.
58. Kojima, A.; Takemoto, T.; Sodeoka, M.; Shibasaki, M. Synthesis 1998, 581-589.
59. Although electronic factors cannot be ruled out in dictating the regioselectivity of the cycloaddition, marked improvement in the regioselectivity observed when an electronically similar TBS group was replaced by a TIPS group indicates that steric effects are predominant.
60. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639-666.
61. Gemal, A. L.; Luche, J.-L. J. Am. Chem. Soc. 1981, 103, 5454-5459.
62. (a) Mitsunobu, O.; Yamada, M. Bull. Chem. Soc. Jpn. 1967, 40, 2380-2382.
63. (b) Mukaiyama, T.; Shintou, T.; Fukumoto, K. J. Am. Chem. Soc. 2003, 125, 10538-10539.
64. Epoxidation attempts with m-CPBA gave a complex mixture of products.
65. VanRheenen, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1976, 17, 1973-1976.
66. Tomioka, K. Synthesis 1990, 541-549.
67. Johnson, R. A,; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993.
68. Andrus, M. B.; Lepore, S. D.; Sclafani, J. A. Tetrahedron Lett. 1997, 38, 4043-4046.
69. Mechanistically, this rearrangement is slightly different from the normal Baeyer-Villiger rearrangement of ketones when m-CPBA is used. For details, see: Cullis, P. M.; Arnold, J. R. P.; Clarke, M.; Howell, R.; DeMira, M.; Naylor, M.; Nicholls, D. J. Chem. Soc., Chem. Commun. 1987, 1088-1089.
70. Amon, C. M.; Banwell, M. G.; Gravatt, G. L. J. Org. Chem. 1987, 52, 4851-4855.
71. For some examples of Baeyer-Villiger rearrangement of vicinal diones to anhydrides, see: (a) Kwart, H.; Wegemer, N. J. J. Am. Chem. Soc. 1961, 83, 2746-2755. (b) Sawaki, Y.; Foote, C. S. J. Am. Chem. Soc. 1979, 101, 6292-6296. (c) Leffler, J. E. J. Org. Chem. 1951, 16, 1785-1787. (d) Hassall, C. H. Org. React. 1957, 9, 73. (e) Jacobs, R. T.; Feutrill, G. I.; Meinwald, J. J. Org. Chem. 1990, 55, 4051-4062. (f) Komarov, I. V.; Monsees, A.; Kadyrov, R.; Fischer, C.; Schmidt, U.; Börner, A. Tetrahedron: Asymmetry 2002, 13, 1615-1620.
72. For some examples of Baeyer-Villiger rearrangement of vicinal diones to anhydrides, see: (a) Kwart, H.; Wegemer, N. J. J. Am. Chem. Soc. 1961, 83, 2746-2755. (b) Sawaki, Y.; Foote, C. S. J. Am. Chem. Soc. 1979, 101, 6292-6296. (c) Leffler, J. E. J. Org. Chem. 1951, 16, 1785-1787. (d) Hassall, C. H. Org. React. 1957, 9, 73. (e) Jacobs, R. T.; Feutrill, G. I.; Meinwald, J. J. Org. Chem. 1990, 55, 4051-4062. (f) Komarov, I. V.; Monsees, A.; Kadyrov, R.; Fischer, C.; Schmidt, U.; Börner, A. Tetrahedron: Asymmetry 2002, 13, 1615-1620.
73. For some examples of Baeyer-Villiger rearrangement of vicinal diones to anhydrides, see: (a) Kwart, H.; Wegemer, N. J. J. Am. Chem. Soc. 1961, 83, 2746-2755. (b) Sawaki, Y.; Foote, C. S. J. Am. Chem. Soc. 1979, 101, 6292-6296. (c) Leffler, J. E. J. Org. Chem. 1951, 16, 1785-1787. (d) Hassall, C. H. Org. React. 1957, 9, 73. (e) Jacobs, R. T.; Feutrill, G. I.; Meinwald, J. J. Org. Chem. 1990, 55, 4051-4062. (f) Komarov, I. V.; Monsees, A.; Kadyrov, R.; Fischer, C.; Schmidt, U.; Börner, A. Tetrahedron: Asymmetry 2002, 13, 1615-1620.
74. For some examples of Baeyer-Villiger rearrangement of vicinal diones to anhydrides, see: (a) Kwart, H.; Wegemer, N. J. J. Am. Chem. Soc. 1961, 83, 2746-2755. (b) Sawaki, Y.; Foote, C. S. J. Am. Chem. Soc. 1979, 101, 6292-6296. (c) Leffler, J. E. J. Org. Chem. 1951, 16, 1785-1787. (d) Hassall, C. H. Org. React. 1957, 9, 73. (e) Jacobs, R. T.; Feutrill, G. I.; Meinwald, J. J. Org. Chem. 1990, 55, 4051-4062. (f) Komarov, I. V.; Monsees, A.; Kadyrov, R.; Fischer, C.; Schmidt, U.; Börner, A. Tetrahedron: Asymmetry 2002, 13, 1615-1620.
75. For some examples of Baeyer-Villiger rearrangement of vicinal diones to anhydrides, see: (a) Kwart, H.; Wegemer, N. J. J. Am. Chem. Soc. 1961, 83, 2746-2755. (b) Sawaki, Y.; Foote, C. S. J. Am. Chem. Soc. 1979, 101, 6292-6296. (c) Leffler, J. E. J. Org. Chem. 1951, 16, 1785-1787. (d) Hassall, C. H. Org. React. 1957, 9, 73. (e) Jacobs, R. T.; Feutrill, G. I.; Meinwald, J. J. Org. Chem. 1990, 55, 4051-4062. (f) Komarov, I. V.; Monsees, A.; Kadyrov, R.; Fischer, C.; Schmidt, U.; Börner, A. Tetrahedron: Asymmetry 2002, 13, 1615-1620.
76. For some examples of Baeyer-Villiger rearrangement of vicinal diones to anhydrides, see: (a) Kwart, H.; Wegemer, N. J. J. Am. Chem. Soc. 1961, 83, 2746-2755. (b) Sawaki, Y.; Foote, C. S. J. Am. Chem. Soc. 1979, 101, 6292-6296. (c) Leffler, J. E. J. Org. Chem. 1951, 16, 1785-1787. (d) Hassall, C. H. Org. React. 1957, 9, 73. (e) Jacobs, R. T.; Feutrill, G. I.; Meinwald, J. J. Org. Chem. 1990, 55, 4051-4062. (f) Komarov, I. V.; Monsees, A.; Kadyrov, R.; Fischer, C.; Schmidt, U.; Börner, A. Tetrahedron: Asymmetry 2002, 13, 1615-1620.
77. A Baeyer-Villiger rearrangement of medium-size cyclic 1,2-diones in the presence of an olefin has been reported but the chemoselectivity was very poor, see: Mayer, W.; Meier, H. Chem. Ber. 1989, 122, 509-517.
78. Miller, R. D.; McKean, D. R. J. Org. Chem. 1981, 46, 2412-2414.
79. Brown, S. P.; Bal, B. S.; Pinnick, H. W. Tetrahedron Lett. 1981, 22, 4891-4894.
80. Buttinelli, P.; Gargaro, G.; Loreto, M. A.; Pellacani, L.; Tardella, P. A. Gazz. Chim. Ital. 1985, 115 (3), 155.
81. Treatment of the lactone 30 with HI indeed gave iodolactone 31 along with recovered starting material, which confirmed that 30 is an intermediate in this tandem lactonization and cyclopropane cleavage.
82. Pearlman, W. M. Tetrahedron Lett. 1967, 8, 1663-1664.
83. Use of other solvents such as ethyl acetate for the hydrogenation completely suppressed the reaction.
84. A detailed study of hydrogenation of bicyclo[n.1.0]alkanes with Pt and Pd/C has been reported, see: Stahl, K.-J.; Hertzsch, W.; Musso, H. Liebigs Ann. Chem. 1985, 1474. A similar regioselectivity preference in the opening of fused cyclopropanes has been observed with Zeise's dimer-catalyst, see: Ma, B.; Snyder, J. K. Org. Lett. 2002, 4, 2731-2734.
85. A detailed study of hydrogenation of bicyclo[n.1.0]alkanes with Pt and Pd/C has been reported, see: Stahl, K.-J.; Hertzsch, W.; Musso, H. Liebigs Ann. Chem. 1985, 1474. A similar regioselectivity preference in the opening of fused cyclopropanes has been observed with Zeise's dimer-catalyst, see: Ma, B.; Snyder, J. K. Org. Lett. 2002, 4, 2731-2734.
86. Molander, G. A.; Hahn, G. J. Org. Chem. 1986, 51, 1135-1138.
87. Redlich, H.; Neumann, H.-J.; Paulsen, H. Chem. Ber. 1977, 110, 2911-2921. For the tributyltin hydride-mediated cleavage of tertiary α-acetoxy carbonyl compounds, see: Grewal, R. S.; Hayes, P. C.; Sawyer, J. F.; Yates, P. J. Chem. Soc., Chem. Commun. 1987, 1290-1292. For the cleavage of benzoates, see: Chen, S.-H.; Wei, J.-M.; Vyas, D. M.; Doyle, T. W.; Farina, V. Tetrahedron Lett. 1993, 34, 6845-6848.
88. Redlich, H.; Neumann, H.-J.; Paulsen, H. Chem. Ber. 1977, 110, 2911-2921. For the tributyltin hydride-mediated cleavage of tertiary α-acetoxy carbonyl compounds, see: Grewal, R. S.; Hayes, P. C.; Sawyer, J. F.; Yates, P. J. Chem. Soc., Chem. Commun. 1987, 1290-1292. For the cleavage of benzoates, see: Chen, S.-H.; Wei, J.-M.; Vyas, D. M.; Doyle, T. W.; Farina, V. Tetrahedron Lett. 1993, 34, 6845-6848.
89. Redlich, H.; Neumann, H.-J.; Paulsen, H. Chem. Ber. 1977, 110, 2911-2921. For the tributyltin hydride-mediated cleavage of tertiary α-acetoxy carbonyl compounds, see: Grewal, R. S.; Hayes, P. C.; Sawyer, J. F.; Yates, P. J. Chem. Soc., Chem. Commun. 1987, 1290-1292. For the cleavage of benzoates, see: Chen, S.-H.; Wei, J.-M.; Vyas, D. M.; Doyle, T. W.; Farina, V. Tetrahedron Lett. 1993, 34, 6845-6848.
90. (a) Barton, D. H. R.; Samadi, M. Tetrahedron 1992, 48, 7083-7090.
91. (b) Anaya, J.; Barton, D. H. R.; Caballero, M. C.; Gero, S. D.; Grande, M.; Laso, N. M.; Hernando, J. I. M. Tetrahedron: Asymmetry 1994, 5, 2137-2140.
92. (a) Trost, B. M. Chem. Rev. 1978, 78, 363-382.
93. (b) Trost, B. M.; Salzmann, T. N.; Hiroi, K. J. Am. Chem. Soc. 1976 98, 4887-4902.
94. 1H NMR data of 9-epi-pentalenic acid, the olefinic proton appeared at δ 6.87, see ref 7i.
95. Youn, I. K.; Yon, G. H.; Pak, C. S. Tetrahedron Lett. 1986, 27, 2409-2410.