Specific C-C Bond Construction by Remote C-H Activation: Synthesis of (-)-trans-Cembranolide

Journal of Organic Chemistry

Volumn 62, Issue 19, 1997, Pages 6603-6607

  Taber, Douglass F ^a   Song, Ying ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CEMBRANOID; DITERPENOID; ESTER DERIVATIVE; FARNESOL; LACTONE DERIVATIVE; TETRAHYDROFURAN;

ARTICLE; CHEMICAL BOND; CYCLIZATION; DIASTEREOISOMER; DRUG ISOLATION; DRUG SYNTHESIS; ENANTIOMER; TRANS ISOMER;

EID: 0030798657     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971065w     Document Type: Article

References (45)

1. For a review of syntheses in the cembranolide series, see: (a) Tius, M. A. Chem. Rev. 1988, 719. For biological activity of cembranolides, see: (b) Manchand, P. S.; White, J. D. Contemporary Bio-organic Chemistry; van Tamelen, E. E., Ed.; Academic: New York, 1978; Vol. 2, p 337. (c) Tursch, B.; Braeckman, J. C.; Daloze, D.; Kaisin, M. Marine Natural Products; Scheuer, P. J., Ed.; Academic: New York, 1978; Vol. II, p 247. (d) Culver, P.; Burch, M.; Potenza, C.; Wasserman, L.; Fenical, W.; Taylor, P. Mol. Pharmacol. 1985, 28, 436. For more recent syntheses in the cembranolide series, see: (e) Marshall, J. A.; DeHoff, B. S. Tetrahedron 1987, 43, 4849. (f) Marshall, J. A.; Crooks, S. L.; DeHoff, B. S. J. Org. Chem. 1988, 53, 1616. (g) Nishitani, K.; Isozaki, M.; Yamakawa, K. Chem. Pharm. Bull. 1990, 38, 28. (h) Paquette, L. A.; Astles, P. C. J. Org. Chem. 1993, 58, 165. (i) Nishitani, K.; Konomi, T.; Okayo, K.; Yamakawa, K. Heterocycles 1994, 37, 679. (j) Rodriguez, A. D.; Pina, I. C.; Barnes, C. L. J. Org, Chem. 1995, 60, 8096. (k) Yue, X.; Li, Y. Tetrahedron Lett. 1996, 37, 671.
2. For a review of syntheses in the cembranolide series, see: (a) Tius, M. A. Chem. Rev. 1988, 719. For biological activity of cembranolides, see: (b) Manchand, P. S.; White, J. D. Contemporary Bio-organic Chemistry; van Tamelen, E. E., Ed.; Academic: New York, 1978; Vol. 2, p 337. (c) Tursch, B.; Braeckman, J. C.; Daloze, D.; Kaisin, M. Marine Natural Products; Scheuer, P. J., Ed.; Academic: New York, 1978; Vol. II, p 247. (d) Culver, P.; Burch, M.; Potenza, C.; Wasserman, L.; Fenical, W.; Taylor, P. Mol. Pharmacol. 1985, 28, 436. For more recent syntheses in the cembranolide series, see: (e) Marshall, J. A.; DeHoff, B. S. Tetrahedron 1987, 43, 4849. (f) Marshall, J. A.; Crooks, S. L.; DeHoff, B. S. J. Org. Chem. 1988, 53, 1616. (g) Nishitani, K.; Isozaki, M.; Yamakawa, K. Chem. Pharm. Bull. 1990, 38, 28. (h) Paquette, L. A.; Astles, P. C. J. Org. Chem. 1993, 58, 165. (i) Nishitani, K.; Konomi, T.; Okayo, K.; Yamakawa, K. Heterocycles 1994, 37, 679. (j) Rodriguez, A. D.; Pina, I. C.; Barnes, C. L. J. Org, Chem. 1995, 60, 8096. (k) Yue, X.; Li, Y. Tetrahedron Lett. 1996, 37, 671.
3. For a review of syntheses in the cembranolide series, see: (a) Tius, M. A. Chem. Rev. 1988, 719. For biological activity of cembranolides, see: (b) Manchand, P. S.; White, J. D. Contemporary Bio-organic Chemistry; van Tamelen, E. E., Ed.; Academic: New York, 1978; Vol. 2, p 337. (c) Tursch, B.; Braeckman, J. C.; Daloze, D.; Kaisin, M. Marine Natural Products; Scheuer, P. J., Ed.; Academic: New York, 1978; Vol. II, p 247. (d) Culver, P.; Burch, M.; Potenza, C.; Wasserman, L.; Fenical, W.; Taylor, P. Mol. Pharmacol. 1985, 28, 436. For more recent syntheses in the cembranolide series, see: (e) Marshall, J. A.; DeHoff, B. S. Tetrahedron 1987, 43, 4849. (f) Marshall, J. A.; Crooks, S. L.; DeHoff, B. S. J. Org. Chem. 1988, 53, 1616. (g) Nishitani, K.; Isozaki, M.; Yamakawa, K. Chem. Pharm. Bull. 1990, 38, 28. (h) Paquette, L. A.; Astles, P. C. J. Org. Chem. 1993, 58, 165. (i) Nishitani, K.; Konomi, T.; Okayo, K.; Yamakawa, K. Heterocycles 1994, 37, 679. (j) Rodriguez, A. D.; Pina, I. C.; Barnes, C. L. J. Org, Chem. 1995, 60, 8096. (k) Yue, X.; Li, Y. Tetrahedron Lett. 1996, 37, 671.
4. For a review of syntheses in the cembranolide series, see: (a) Tius, M. A. Chem. Rev. 1988, 719. For biological activity of cembranolides, see: (b) Manchand, P. S.; White, J. D. Contemporary Bio-organic Chemistry; van Tamelen, E. E., Ed.; Academic: New York, 1978; Vol. 2, p 337. (c) Tursch, B.; Braeckman, J. C.; Daloze, D.; Kaisin, M. Marine Natural Products; Scheuer, P. J., Ed.; Academic: New York, 1978; Vol. II, p 247. (d) Culver, P.; Burch, M.; Potenza, C.; Wasserman, L.; Fenical, W.; Taylor, P. Mol. Pharmacol. 1985, 28, 436. For more recent syntheses in the cembranolide series, see: (e) Marshall, J. A.; DeHoff, B. S. Tetrahedron 1987, 43, 4849. (f) Marshall, J. A.; Crooks, S. L.; DeHoff, B. S. J. Org. Chem. 1988, 53, 1616. (g) Nishitani, K.; Isozaki, M.; Yamakawa, K. Chem. Pharm. Bull. 1990, 38, 28. (h) Paquette, L. A.; Astles, P. C. J. Org. Chem. 1993, 58, 165. (i) Nishitani, K.; Konomi, T.; Okayo, K.; Yamakawa, K. Heterocycles 1994, 37, 679. (j) Rodriguez, A. D.; Pina, I. C.; Barnes, C. L. J. Org, Chem. 1995, 60, 8096. (k) Yue, X.; Li, Y. Tetrahedron Lett. 1996, 37, 671.
5. For a review of syntheses in the cembranolide series, see: (a) Tius, M. A. Chem. Rev. 1988, 719. For biological activity of cembranolides, see: (b) Manchand, P. S.; White, J. D. Contemporary Bio-organic Chemistry; van Tamelen, E. E., Ed.; Academic: New York, 1978; Vol. 2, p 337. (c) Tursch, B.; Braeckman, J. C.; Daloze, D.; Kaisin, M. Marine Natural Products; Scheuer, P. J., Ed.; Academic: New York, 1978; Vol. II, p 247. (d) Culver, P.; Burch, M.; Potenza, C.; Wasserman, L.; Fenical, W.; Taylor, P. Mol. Pharmacol. 1985, 28, 436. For more recent syntheses in the cembranolide series, see: (e) Marshall, J. A.; DeHoff, B. S. Tetrahedron 1987, 43, 4849. (f) Marshall, J. A.; Crooks, S. L.; DeHoff, B. S. J. Org. Chem. 1988, 53, 1616. (g) Nishitani, K.; Isozaki, M.; Yamakawa, K. Chem. Pharm. Bull. 1990, 38, 28. (h) Paquette, L. A.; Astles, P. C. J. Org. Chem. 1993, 58, 165. (i) Nishitani, K.; Konomi, T.; Okayo, K.; Yamakawa, K. Heterocycles 1994, 37, 679. (j) Rodriguez, A. D.; Pina, I. C.; Barnes, C. L. J. Org, Chem. 1995, 60, 8096. (k) Yue, X.; Li, Y. Tetrahedron Lett. 1996, 37, 671.
6. For a review of syntheses in the cembranolide series, see: (a) Tius, M. A. Chem. Rev. 1988, 719. For biological activity of cembranolides, see: (b) Manchand, P. S.; White, J. D. Contemporary Bio-organic Chemistry; van Tamelen, E. E., Ed.; Academic: New York, 1978; Vol. 2, p 337. (c) Tursch, B.; Braeckman, J. C.; Daloze, D.; Kaisin, M. Marine Natural Products; Scheuer, P. J., Ed.; Academic: New York, 1978; Vol. II, p 247. (d) Culver, P.; Burch, M.; Potenza, C.; Wasserman, L.; Fenical, W.; Taylor, P. Mol. Pharmacol. 1985, 28, 436. For more recent syntheses in the cembranolide series, see: (e) Marshall, J. A.; DeHoff, B. S. Tetrahedron 1987, 43, 4849. (f) Marshall, J. A.; Crooks, S. L.; DeHoff, B. S. J. Org. Chem. 1988, 53, 1616. (g) Nishitani, K.; Isozaki, M.; Yamakawa, K. Chem. Pharm. Bull. 1990, 38, 28. (h) Paquette, L. A.; Astles, P. C. J. Org. Chem. 1993, 58, 165. (i) Nishitani, K.; Konomi, T.; Okayo, K.; Yamakawa, K. Heterocycles 1994, 37, 679. (j) Rodriguez, A. D.; Pina, I. C.; Barnes, C. L. J. Org, Chem. 1995, 60, 8096. (k) Yue, X.; Li, Y. Tetrahedron Lett. 1996, 37, 671.
7. For a review of syntheses in the cembranolide series, see: (a) Tius, M. A. Chem. Rev. 1988, 719. For biological activity of cembranolides, see: (b) Manchand, P. S.; White, J. D. Contemporary Bio-organic Chemistry; van Tamelen, E. E., Ed.; Academic: New York, 1978; Vol. 2, p 337. (c) Tursch, B.; Braeckman, J. C.; Daloze, D.; Kaisin, M. Marine Natural Products; Scheuer, P. J., Ed.; Academic: New York, 1978; Vol. II, p 247. (d) Culver, P.; Burch, M.; Potenza, C.; Wasserman, L.; Fenical, W.; Taylor, P. Mol. Pharmacol. 1985, 28, 436. For more recent syntheses in the cembranolide series, see: (e) Marshall, J. A.; DeHoff, B. S. Tetrahedron 1987, 43, 4849. (f) Marshall, J. A.; Crooks, S. L.; DeHoff, B. S. J. Org. Chem. 1988, 53, 1616. (g) Nishitani, K.; Isozaki, M.; Yamakawa, K. Chem. Pharm. Bull. 1990, 38, 28. (h) Paquette, L. A.; Astles, P. C. J. Org. Chem. 1993, 58, 165. (i) Nishitani, K.; Konomi, T.; Okayo, K.; Yamakawa, K. Heterocycles 1994, 37, 679. (j) Rodriguez, A. D.; Pina, I. C.; Barnes, C. L. J. Org, Chem. 1995, 60, 8096. (k) Yue, X.; Li, Y. Tetrahedron Lett. 1996, 37, 671.
8. For a review of syntheses in the cembranolide series, see: (a) Tius, M. A. Chem. Rev. 1988, 719. For biological activity of cembranolides, see: (b) Manchand, P. S.; White, J. D. Contemporary Bio-organic Chemistry; van Tamelen, E. E., Ed.; Academic: New York, 1978; Vol. 2, p 337. (c) Tursch, B.; Braeckman, J. C.; Daloze, D.; Kaisin, M. Marine Natural Products; Scheuer, P. J., Ed.; Academic: New York, 1978; Vol. II, p 247. (d) Culver, P.; Burch, M.; Potenza, C.; Wasserman, L.; Fenical, W.; Taylor, P. Mol. Pharmacol. 1985, 28, 436. For more recent syntheses in the cembranolide series, see: (e) Marshall, J. A.; DeHoff, B. S. Tetrahedron 1987, 43, 4849. (f) Marshall, J. A.; Crooks, S. L.; DeHoff, B. S. J. Org. Chem. 1988, 53, 1616. (g) Nishitani, K.; Isozaki, M.; Yamakawa, K. Chem. Pharm. Bull. 1990, 38, 28. (h) Paquette, L. A.; Astles, P. C. J. Org. Chem. 1993, 58, 165. (i) Nishitani, K.; Konomi, T.; Okayo, K.; Yamakawa, K. Heterocycles 1994, 37, 679. (j) Rodriguez, A. D.; Pina, I. C.; Barnes, C. L. J. Org, Chem. 1995, 60, 8096. (k) Yue, X.; Li, Y. Tetrahedron Lett. 1996, 37, 671.
9. For a review of syntheses in the cembranolide series, see: (a) Tius, M. A. Chem. Rev. 1988, 719. For biological activity of cembranolides, see: (b) Manchand, P. S.; White, J. D. Contemporary Bio-organic Chemistry; van Tamelen, E. E., Ed.; Academic: New York, 1978; Vol. 2, p 337. (c) Tursch, B.; Braeckman, J. C.; Daloze, D.; Kaisin, M. Marine Natural Products; Scheuer, P. J., Ed.; Academic: New York, 1978; Vol. II, p 247. (d) Culver, P.; Burch, M.; Potenza, C.; Wasserman, L.; Fenical, W.; Taylor, P. Mol. Pharmacol. 1985, 28, 436. For more recent syntheses in the cembranolide series, see: (e) Marshall, J. A.; DeHoff, B. S. Tetrahedron 1987, 43, 4849. (f) Marshall, J. A.; Crooks, S. L.; DeHoff, B. S. J. Org. Chem. 1988, 53, 1616. (g) Nishitani, K.; Isozaki, M.; Yamakawa, K. Chem. Pharm. Bull. 1990, 38, 28. (h) Paquette, L. A.; Astles, P. C. J. Org. Chem. 1993, 58, 165. (i) Nishitani, K.; Konomi, T.; Okayo, K.; Yamakawa, K. Heterocycles 1994, 37, 679. (j) Rodriguez, A. D.; Pina, I. C.; Barnes, C. L. J. Org, Chem. 1995, 60, 8096. (k) Yue, X.; Li, Y. Tetrahedron Lett. 1996, 37, 671.
10. For a review of syntheses in the cembranolide series, see: (a) Tius, M. A. Chem. Rev. 1988, 719. For biological activity of cembranolides, see: (b) Manchand, P. S.; White, J. D. Contemporary Bio-organic Chemistry; van Tamelen, E. E., Ed.; Academic: New York, 1978; Vol. 2, p 337. (c) Tursch, B.; Braeckman, J. C.; Daloze, D.; Kaisin, M. Marine Natural Products; Scheuer, P. J., Ed.; Academic: New York, 1978; Vol. II, p 247. (d) Culver, P.; Burch, M.; Potenza, C.; Wasserman, L.; Fenical, W.; Taylor, P. Mol. Pharmacol. 1985, 28, 436. For more recent syntheses in the cembranolide series, see: (e) Marshall, J. A.; DeHoff, B. S. Tetrahedron 1987, 43, 4849. (f) Marshall, J. A.; Crooks, S. L.; DeHoff, B. S. J. Org. Chem. 1988, 53, 1616. (g) Nishitani, K.; Isozaki, M.; Yamakawa, K. Chem. Pharm. Bull. 1990, 38, 28. (h) Paquette, L. A.; Astles, P. C. J. Org. Chem. 1993, 58, 165. (i) Nishitani, K.; Konomi, T.; Okayo, K.; Yamakawa, K. Heterocycles 1994, 37, 679. (j) Rodriguez, A. D.; Pina, I. C.; Barnes, C. L. J. Org, Chem. 1995, 60, 8096. (k) Yue, X.; Li, Y. Tetrahedron Lett. 1996, 37, 671.
11. For a review of syntheses in the cembranolide series, see: (a) Tius, M. A. Chem. Rev. 1988, 719. For biological activity of cembranolides, see: (b) Manchand, P. S.; White, J. D. Contemporary Bio-organic Chemistry; van Tamelen, E. E., Ed.; Academic: New York, 1978; Vol. 2, p 337. (c) Tursch, B.; Braeckman, J. C.; Daloze, D.; Kaisin, M. Marine Natural Products; Scheuer, P. J., Ed.; Academic: New York, 1978; Vol. II, p 247. (d) Culver, P.; Burch, M.; Potenza, C.; Wasserman, L.; Fenical, W.; Taylor, P. Mol. Pharmacol. 1985, 28, 436. For more recent syntheses in the cembranolide series, see: (e) Marshall, J. A.; DeHoff, B. S. Tetrahedron 1987, 43, 4849. (f) Marshall, J. A.; Crooks, S. L.; DeHoff, B. S. J. Org. Chem. 1988, 53, 1616. (g) Nishitani, K.; Isozaki, M.; Yamakawa, K. Chem. Pharm. Bull. 1990, 38, 28. (h) Paquette, L. A.; Astles, P. C. J. Org. Chem. 1993, 58, 165. (i) Nishitani, K.; Konomi, T.; Okayo, K.; Yamakawa, K. Heterocycles 1994, 37, 679. (j) Rodriguez, A. D.; Pina, I. C.; Barnes, C. L. J. Org, Chem. 1995, 60, 8096. (k) Yue, X.; Li, Y. Tetrahedron Lett. 1996, 37, 671.
12. Uchio, Y.; Eguchi, S.; Nakayama, M.; Hase, T. Chem. Lett. 1982, 277.
13. Kodama, M.; Takahashi, T.; Ito, S. Tetrahedron Lett. 1982, 23, 5175.
14. Nishitani, K.; Konomi, T.; Okada, K.; Yamakawa, K. Heterocycles 1994, 37, 679.
15. For C-C bond construction by intermolecular C-H activation, see: (a) Gong, J.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118, 4486. (b) Xiang, J.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118, 11986. For a review of diastereoselectivity and enantioselectivity in C-C bond construction by intramolecular C-H activation, see: (b) Taber, D. F. Methods of Organic Chemistry; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Georg Thieme Verlag Stuttgart: New York, 1995; p 1127. For more recent references, see: (c) McCarthy, N.; N.; McKervey, M. A.; Ye, T.; McCann, M.; Murphy, E.; Doyle, M. P. Tetrahedron Lett. 1992, 33, 5983. (d) Taber, D. F.; You, K. K.; Rheingold, A. L. J. Am. Chem. Soc. 1996, 118, 547. (e) Doyle, M. P.; Kalinin, A. V.; Ene, D. G. J. Am. Chem. Soc. 1996, 118, 8837. (f) Ogawa, T.; Ohtake, Y.; Ikegami, S.; Hashimoto, S. Synlett. 1996, 85. (g) Wee, A. G. H.; Liu, B. Tetrahedron Lett. 1996, 37, 145.
16. For C-C bond construction by intermolecular C-H activation, see: (a) Gong, J.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118, 4486. (b) Xiang, J.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118, 11986. For a review of diastereoselectivity and enantioselectivity in C-C bond construction by intramolecular C-H activation, see: (b) Taber, D. F. Methods of Organic Chemistry; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Georg Thieme Verlag Stuttgart: New York, 1995; p 1127. For more recent references, see: (c) McCarthy, N.; N.; McKervey, M. A.; Ye, T.; McCann, M.; Murphy, E.; Doyle, M. P. Tetrahedron Lett. 1992, 33, 5983. (d) Taber, D. F.; You, K. K.; Rheingold, A. L. J. Am. Chem. Soc. 1996, 118, 547. (e) Doyle, M. P.; Kalinin, A. V.; Ene, D. G. J. Am. Chem. Soc. 1996, 118, 8837. (f) Ogawa, T.; Ohtake, Y.; Ikegami, S.; Hashimoto, S. Synlett. 1996, 85. (g) Wee, A. G. H.; Liu, B. Tetrahedron Lett. 1996, 37, 145.
17. For C-C bond construction by intermolecular C-H activation, see: (a) Gong, J.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118, 4486. (b) Xiang, J.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118, 11986. For a review of diastereoselectivity and enantioselectivity in C-C bond construction by intramolecular C-H activation, see: (b) Taber, D. F. Methods of Organic Chemistry; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Georg Thieme Verlag Stuttgart: New York, 1995; p 1127. For more recent references, see: (c) McCarthy, N.; N.; McKervey, M. A.; Ye, T.; McCann, M.; Murphy, E.; Doyle, M. P. Tetrahedron Lett. 1992, 33, 5983. (d) Taber, D. F.; You, K. K.; Rheingold, A. L. J. Am. Chem. Soc. 1996, 118, 547. (e) Doyle, M. P.; Kalinin, A. V.; Ene, D. G. J. Am. Chem. Soc. 1996, 118, 8837. (f) Ogawa, T.; Ohtake, Y.; Ikegami, S.; Hashimoto, S. Synlett. 1996, 85. (g) Wee, A. G. H.; Liu, B. Tetrahedron Lett. 1996, 37, 145.
18. For C-C bond construction by intermolecular C-H activation, see: (a) Gong, J.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118, 4486. (b) Xiang, J.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118, 11986. For a review of diastereoselectivity and enantioselectivity in C-C bond construction by intramolecular C-H activation, see: (b) Taber, D. F. Methods of Organic Chemistry; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Georg Thieme Verlag Stuttgart: New York, 1995; p 1127. For more recent references, see: (c) McCarthy, N.; N.; McKervey, M. A.; Ye, T.; McCann, M.; Murphy, E.; Doyle, M. P. Tetrahedron Lett. 1992, 33, 5983. (d) Taber, D. F.; You, K. K.; Rheingold, A. L. J. Am. Chem. Soc. 1996, 118, 547. (e) Doyle, M. P.; Kalinin, A. V.; Ene, D. G. J. Am. Chem. Soc. 1996, 118, 8837. (f) Ogawa, T.; Ohtake, Y.; Ikegami, S.; Hashimoto, S. Synlett. 1996, 85. (g) Wee, A. G. H.; Liu, B. Tetrahedron Lett. 1996, 37, 145.
19. For C-C bond construction by intermolecular C-H activation, see: (a) Gong, J.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118, 4486. (b) Xiang, J.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118, 11986. For a review of diastereoselectivity and enantioselectivity in C-C bond construction by intramolecular C-H activation, see: (b) Taber, D. F. Methods of Organic Chemistry; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Georg Thieme Verlag Stuttgart: New York, 1995; p 1127. For more recent references, see: (c) McCarthy, N.; N.; McKervey, M. A.; Ye, T.; McCann, M.; Murphy, E.; Doyle, M. P. Tetrahedron Lett. 1992, 33, 5983. (d) Taber, D. F.; You, K. K.; Rheingold, A. L. J. Am. Chem. Soc. 1996, 118, 547. (e) Doyle, M. P.; Kalinin, A. V.; Ene, D. G. J. Am. Chem. Soc. 1996, 118, 8837. (f) Ogawa, T.; Ohtake, Y.; Ikegami, S.; Hashimoto, S. Synlett. 1996, 85. (g) Wee, A. G. H.; Liu, B. Tetrahedron Lett. 1996, 37, 145.
20. For C-C bond construction by intermolecular C-H activation, see: (a) Gong, J.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118, 4486. (b) Xiang, J.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118, 11986. For a review of diastereoselectivity and enantioselectivity in C-C bond construction by intramolecular C-H activation, see: (b) Taber, D. F. Methods of Organic Chemistry; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Georg Thieme Verlag Stuttgart: New York, 1995; p 1127. For more recent references, see: (c) McCarthy, N.; N.; McKervey, M. A.; Ye, T.; McCann, M.; Murphy, E.; Doyle, M. P. Tetrahedron Lett. 1992, 33, 5983. (d) Taber, D. F.; You, K. K.; Rheingold, A. L. J. Am. Chem. Soc. 1996, 118, 547. (e) Doyle, M. P.; Kalinin, A. V.; Ene, D. G. J. Am. Chem. Soc. 1996, 118, 8837. (f) Ogawa, T.; Ohtake, Y.; Ikegami, S.; Hashimoto, S. Synlett. 1996, 85. (g) Wee, A. G. H.; Liu, B. Tetrahedron Lett. 1996, 37, 145.
21. For C-C bond construction by intermolecular C-H activation, see: (a) Gong, J.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118, 4486. (b) Xiang, J.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118, 11986. For a review of diastereoselectivity and enantioselectivity in C-C bond construction by intramolecular C-H activation, see: (b) Taber, D. F. Methods of Organic Chemistry; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Georg Thieme Verlag Stuttgart: New York, 1995; p 1127. For more recent references, see: (c) McCarthy, N.; N.; McKervey, M. A.; Ye, T.; McCann, M.; Murphy, E.; Doyle, M. P. Tetrahedron Lett. 1992, 33, 5983. (d) Taber, D. F.; You, K. K.; Rheingold, A. L. J. Am. Chem. Soc. 1996, 118, 547. (e) Doyle, M. P.; Kalinin, A. V.; Ene, D. G. J. Am. Chem. Soc. 1996, 118, 8837. (f) Ogawa, T.; Ohtake, Y.; Ikegami, S.; Hashimoto, S. Synlett. 1996, 85. (g) Wee, A. G. H.; Liu, B. Tetrahedron Lett. 1996, 37, 145.
22. For C-C bond construction by intermolecular C-H activation, see: (a) Gong, J.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118, 4486. (b) Xiang, J.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118, 11986. For a review of diastereoselectivity and enantioselectivity in C-C bond construction by intramolecular C-H activation, see: (b) Taber, D. F. Methods of Organic Chemistry; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Georg Thieme Verlag Stuttgart: New York, 1995; p 1127. For more recent references, see: (c) McCarthy, N.; N.; McKervey, M. A.; Ye, T.; McCann, M.; Murphy, E.; Doyle, M. P. Tetrahedron Lett. 1992, 33, 5983. (d) Taber, D. F.; You, K. K.; Rheingold, A. L. J. Am. Chem. Soc. 1996, 118, 547. (e) Doyle, M. P.; Kalinin, A. V.; Ene, D. G. J. Am. Chem. Soc. 1996, 118, 8837. (f) Ogawa, T.; Ohtake, Y.; Ikegami, S.; Hashimoto, S. Synlett. 1996, 85. (g) Wee, A. G. H.; Liu, B. Tetrahedron Lett. 1996, 37, 145.
23. (a) Breslow, R.; Baldwin, S.; Fiechtner, T.; Kalicky, P.; Liu, S.; Washburn, W. J. Am. Chem. Soc. 1973, 95, 3251.
24. (b) Breslow, R.; Corcoran, R. J.; Snider, B. B J. Am. Chem. Soc. 1974, 96, 6791.
25. (c) Breslow, R.; Rothbard, J.; Herman, F.; Rodriguez, M. L. J. Am. Chem. Soc. 1978, 100, 1213.
26. (a) Taber, D. F.; Song, Y. Tetrahedron Lett. 1995, 36, 2578.
27. (b) Taber, D. F.; Song, Y. J. Org. Chem. 1996, 61, 6706.
28. (-)-(R)-1,2-epoxy-3-(benzyloxy)propane was provided by DAISO Co., Ltd.
29. For the preparation of acetophenone dimethylhydrazone, see: (a) Fisher, M.; Fisher, L. Reagents for Organic Synthesis; John Wiley & Sons: New York, 1969; Vol. 2; p 154. For the deprotonation of dimethylhydrazones, see: (b) Enders D.; Weuster, P. Tetrahedron Lett. 1978, 19, 2853.
30. For the preparation of acetophenone dimethylhydrazone, see: (a) Fisher, M.; Fisher, L. Reagents for Organic Synthesis; John Wiley & Sons: New York, 1969; Vol. 2; p 154. For the deprotonation of dimethylhydrazones, see: (b) Enders D.; Weuster, P. Tetrahedron Lett. 1978, 19, 2853.
31. Crotti, P.; Bussolo, V. D.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 1994, 35, 6537.
32. Castro, A.; Spencer, T. A. J. Org. Chem. 1992, 57, 3496.
33. Taber, D. F.; You, K.; Song, Y. J. Org. Chem. 1995, 60, 1093.
34. Forsey, S. P.; Rajapaksa, D.; Taylor, N. J.; Rodrigo, R. J. Org. Chem. 1989, 54, 4280. It is noteworthy that β-elimination/cyclization, which would lead to all four diastereomers of 3, does not compete with this epimerization.
35. Sharpless, K. B.; Umbreit, M. A. J. Am. Chem. Soc. 1977, 99, 5526.
36. Rosen, T.; Taschner, M. J.; Thomas, J. A.; Heathcock, C. H. J. Org. Chem. 1985, 50, 1190.
37. (a) Kumagai, T.; Ise, F.; Uyehara, T.; Kato, T. Chem. Lett. 1981, 25.
38. (b) Takayanagi, H.; Uyehara, T.; Kato, T. Chem. Commun. 1978, 359.
39. (a) Marshall, J. A.; Cleary, D. G. J. Org. Chem. 1986, 51, 858.
40. (b) For a closely related cyclization/desulfonylation/debenzylation, see: Miyaoka, H.; Saka, Y.; Miura, S.; Yamada, Y. Tetrahedron Lett. 1996, 37, 7107.
41. Kim, J. N.; Ryu, E. K. Tetrahedron Lett. 1992, 33, 3141.
42. Taber, D. F.; Song, Y. J. Org. Chem. 1996, 61, 7508.
43. (a) Ziegler, F. E.; Fang, J. M. J. Org. Chem. 1981, 46, 825.
44. (b) Ziegler, F. E.; Fang, J. M.; Tam, C. C. J. Am. Chem. Soc. 1982, 104, 7174.
45. For general experimental procedures, see: Taber, D. F.; Meagley, R. P.; Doren, D. J. J. Org. Chem. 1996, 61, 5723.