Novel isobenzofuran generation from silylated lactol leading to desilylated or silylated adducts depending on the choice of metal fluorides

Synlett

Volumn , Issue 11, 2002, Pages 1868-1870

  Ohmura, Hirofumi ^a   Mikami, Koichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Carbonyl ylides; Isobenzofuran; Metal fluorides; Silylated isobenzofuran adducts; Silylated lactol

Indexed keywords

CARBONYL DERIVATIVE; DICARBOXYLIC ACID DERIVATIVE; DIMETHYLACETYLENE DICARBOXYLATE; FLUORIDE; ISOBENZOFURAN DERIVATIVE; METAL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; METHODOLOGY; REACTION ANALYSIS; SILYLATION; SYNTHESIS;

EID: 0036425602     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34871     Document Type: Article

References (35)

1. Reviews: (a) Padwa, A. In Comprehensive Organic Synthesis, Vol. 4; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991, 1089-1093. (b) Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263. (c) Ye, T.; Mckervey, M. A. Chem. Rev. 1994, 94, 1091. (d) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. (e) Oku, A.; Mori, T.; Sawada, Y. J. Synth. Org. Chem. Jpn. 2000, 58, 934.
2. Reviews: (a) Padwa, A. In Comprehensive Organic Synthesis, Vol. 4; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991, 1089-1093. (b) Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263. (c) Ye, T.; Mckervey, M. A. Chem. Rev. 1994, 94, 1091. (d) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. (e) Oku, A.; Mori, T.; Sawada, Y. J. Synth. Org. Chem. Jpn. 2000, 58, 934.
3. Reviews: (a) Padwa, A. In Comprehensive Organic Synthesis, Vol. 4; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991, 1089-1093. (b) Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263. (c) Ye, T.; Mckervey, M. A. Chem. Rev. 1994, 94, 1091. (d) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. (e) Oku, A.; Mori, T.; Sawada, Y. J. Synth. Org. Chem. Jpn. 2000, 58, 934.
4. Reviews: (a) Padwa, A. In Comprehensive Organic Synthesis, Vol. 4; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991, 1089-1093. (b) Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263. (c) Ye, T.; Mckervey, M. A. Chem. Rev. 1994, 94, 1091. (d) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. (e) Oku, A.; Mori, T.; Sawada, Y. J. Synth. Org. Chem. Jpn. 2000, 58, 934.
5. Reviews: (a) Padwa, A. In Comprehensive Organic Synthesis, Vol. 4; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991, 1089-1093. (b) Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263. (c) Ye, T.; Mckervey, M. A. Chem. Rev. 1994, 94, 1091. (d) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. (e) Oku, A.; Mori, T.; Sawada, Y. J. Synth. Org. Chem. Jpn. 2000, 58, 934.
6. Reviews: (a) Haddadin, M. J. Heterocycles 1978, 9, 865. (b) Friedrichsen, W. Adv. Heterocyclic Chem. 1980, 26, 135. (c) Wiersum, U. E. Aldrichim. Acta. 1981, 14, 53. (d) Rodrigo, R. Tetrathedron 1988, 44, 2093. (e) Hosomi, A. J. Synth. Org. Chem., Jpn. 1998, 56, 681.
7. Reviews: (a) Haddadin, M. J. Heterocycles 1978, 9, 865. (b) Friedrichsen, W. Adv. Heterocyclic Chem. 1980, 26, 135. (c) Wiersum, U. E. Aldrichim. Acta. 1981, 14, 53. (d) Rodrigo, R. Tetrathedron 1988, 44, 2093. (e) Hosomi, A. J. Synth. Org. Chem., Jpn. 1998, 56, 681.
8. Reviews: (a) Haddadin, M. J. Heterocycles 1978, 9, 865. (b) Friedrichsen, W. Adv. Heterocyclic Chem. 1980, 26, 135. (c) Wiersum, U. E. Aldrichim. Acta 1981, 14, 53. (d) Rodrigo, R. Tetrathedron 1988, 44, 2093. (e) Hosomi, A. J. Synth. Org. Chem., Jpn. 1998, 56, 681.
9. Reviews: (a) Haddadin, M. J. Heterocycles 1978, 9, 865. (b) Friedrichsen, W. Adv. Heterocyclic Chem. 1980, 26, 135. (c) Wiersum, U. E. Aldrichim. Acta 1981, 14, 53. (d) Rodrigo, R. Tetrathedron 1988, 44, 2093. (e) Hosomi, A. J. Synth. Org. Chem., Jpn. 1998, 56, 681.
10. Reviews: (a) Haddadin, M. J. Heterocycles 1978, 9, 865. (b) Friedrichsen, W. Adv. Heterocyclic Chem. 1980, 26, 135. (c) Wiersum, U. E. Aldrichim. Acta 1981, 14, 53. (d) Rodrigo, R. Tetrathedron 1988, 44, 2093. (e) Hosomi, A. J. Synth. Org. Chem., Jpn. 1998, 56, 681.
11. Representative methods for isobenzofuran generation: (a) Wiersum, U. E.; Mijs, W. J. J. Chem. Soc., Chem. Commun. 1972, 347. (b) Plaumann, H. P.; Smith, J. G.; Rodrigo, R. J. Chem. Soc. Chem. Commun. 1980, 354. (c) Tobia, D.; Rickborn, B. J. Org. Chem. 1986, 51, 3849. (d) Hamaguchi, M.; Ibata, T. Chem. Lett. 1976, 287. (e) Hayakawa, K.; Yamaguchi, Y.; Kanematsu, K. Tetrahedron Lett. 1985, 26, 2689.
12. Representative methods for isobenzofuran generation: (a) Wiersum, U. E.; Mijs, W. J. J. Chem. Soc., Chem. Commun. 1972, 347. (b) Plaumann, H. P.; Smith, J. G.; Rodrigo, R. J. Chem. Soc. Chem. Commun. 1980, 354. (c) Tobia, D.; Rickborn, B. J. Org. Chem. 1986, 51, 3849. (d) Hamaguchi, M.; Ibata, T. Chem. Lett. 1976, 287. (e) Hayakawa, K.; Yamaguchi, Y.; Kanematsu, K. Tetrahedron Lett. 1985, 26, 2689.
13. Representative methods for isobenzofuran generation: (a) Wiersum, U. E.; Mijs, W. J. J. Chem. Soc., Chem. Commun. 1972, 347. (b) Plaumann, H. P.; Smith, J. G.; Rodrigo, R. J. Chem. Soc. Chem. Commun. 1980, 354. (c) Tobia, D.; Rickborn, B. J. Org. Chem. 1986, 51, 3849. (d) Hamaguchi, M.; Ibata, T. Chem. Lett. 1976, 287. (e) Hayakawa, K.; Yamaguchi, Y.; Kanematsu, K. Tetrahedron Lett. 1985, 26, 2689.
14. Representative methods for isobenzofuran generation: (a) Wiersum, U. E.; Mijs, W. J. J. Chem. Soc., Chem. Commun. 1972, 347. (b) Plaumann, H. P.; Smith, J. G.; Rodrigo, R. J. Chem. Soc. Chem. Commun. 1980, 354. (c) Tobia, D.; Rickborn, B. J. Org. Chem. 1986, 51, 3849. (d) Hamaguchi, M.; Ibata, T. Chem. Lett. 1976, 287. (e) Hayakawa, K.; Yamaguchi, Y.; Kanematsu, K. Tetrahedron Lett. 1985, 26, 2689.
15. Representative methods for isobenzofuran generation: (a) Wiersum, U. E.; Mijs, W. J. J. Chem. Soc., Chem. Commun. 1972, 347. (b) Plaumann, H. P.; Smith, J. G.; Rodrigo, R. J. Chem. Soc. Chem. Commun. 1980, 354. (c) Tobia, D.; Rickborn, B. J. Org. Chem. 1986, 51, 3849. (d) Hamaguchi, M.; Ibata, T. Chem. Lett. 1976, 287. (e) Hayakawa, K.; Yamaguchi, Y.; Kanematsu, K. Tetrahedron Lett. 1985, 26, 2689.
16. (2,5) Ene cyclization: (a) Ohmura, H.; Smyth, G. D.; Mikami, K. J. Org. Chem. 1999, 64, 6056. (b) Ohmura, H.; Mikami, K. Tetrahedron Lett. 2001, 42, 6859.
17. (2,5) Ene cyclization: (a) Ohmura, H.; Smyth, G. D.; Mikami, K. J. Org. Chem. 1999, 64, 6056. (b) Ohmura, H.; Mikami, K. Tetrahedron Lett. 2001, 42, 6859.
18. Review on 1-(m,n) terminology: Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021.
19. Account on 1-(m,n) terminology: Sarkar, T. K. J. Indian Inst. Sci. 1994, 74, 329.
20. Recent examples of 1-(m,n) ene cyclization: (a) Loh, T.-P.; Hu, Q.-Y.; Tan, K.-T.; Cheng, H.-S. Org. Lett. 2001, 3, 2669. (b) Okano, T.; Nakagawa, K.; Kubodera, N.; Ozono, K.; Isaka, A.; Osawa, A.; Terada, M.; Mikami, K. Chem. Biol. 2000, 7, 173. (c) Mikami, K.; Osawa, A.; Isaka, A.; Sawa, E.; Shimizu, M.; Terada, M.; Kubodera, N.; Nakagawa, K.; Tsugawa, N.; Okano, T. Tetrahedron Lett. 1998, 39, 3359. (d) Noguchi, M.; Mizukoshi, T.; Nishimura, S. Bull. Chem. Soc. Jpn. 1997, 70, 2201.
21. Recent examples of 1-(m,n) ene cyclization: (a) Loh, T.-P.; Hu, Q.-Y.; Tan, K.-T.; Cheng, H.-S. Org. Lett. 2001, 3, 2669. (b) Okano, T.; Nakagawa, K.; Kubodera, N.; Ozono, K.; Isaka, A.; Osawa, A.; Terada, M.; Mikami, K. Chem. Biol. 2000, 7, 173. (c) Mikami, K.; Osawa, A.; Isaka, A.; Sawa, E.; Shimizu, M.; Terada, M.; Kubodera, N.; Nakagawa, K.; Tsugawa, N.; Okano, T. Tetrahedron Lett. 1998, 39, 3359. (d) Noguchi, M.; Mizukoshi, T.; Nishimura, S. Bull. Chem. Soc. Jpn. 1997, 70, 2201.
22. Recent examples of 1-(m,n) ene cyclization: (a) Loh, T.-P.; Hu, Q.-Y.; Tan, K.-T.; Cheng, H.-S. Org. Lett. 2001, 3, 2669. (b) Okano, T.; Nakagawa, K.; Kubodera, N.; Ozono, K.; Isaka, A.; Osawa, A.; Terada, M.; Mikami, K. Chem. Biol. 2000, 7, 173. (c) Mikami, K.; Osawa, A.; Isaka, A.; Sawa, E.; Shimizu, M.; Terada, M.; Kubodera, N.; Nakagawa, K.; Tsugawa, N.; Okano, T. Tetrahedron Lett. 1998, 39, 3359. (d) Noguchi, M.; Mizukoshi, T.; Nishimura, S. Bull. Chem. Soc. Jpn. 1997, 70, 2201.
23. Recent examples of 1-(m,n) ene cyclization: (a) Loh, T.-P.; Hu, Q.-Y.; Tan, K.-T.; Cheng, H.-S. Org. Lett. 2001, 3, 2669. (b) Okano, T.; Nakagawa, K.; Kubodera, N.; Ozono, K.; Isaka, A.; Osawa, A.; Terada, M.; Mikami, K. Chem. Biol. 2000, 7, 173. (c) Mikami, K.; Osawa, A.; Isaka, A.; Sawa, E.; Shimizu, M.; Terada, M.; Kubodera, N.; Nakagawa, K.; Tsugawa, N.; Okano, T. Tetrahedron Lett. 1998, 39, 3359. (d) Noguchi, M.; Mizukoshi, T.; Nishimura, S. Bull. Chem. Soc. Jpn. 1997, 70, 2201.
24. Reviews on sequential reactions: (a) Nakai, T.; Mikami, K. Kagaku no Ryoiki 1982, 36, 661; Chem. Abstr. 1982, 96, 16001. (b) Ziegler, F. E. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 875. (c) Ho, T.-L. Tandem Organic Reactions; Wiley: New York, 1992. (d) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131. (e) Special issue on frontiers in organic reaction sequence: Wender, P. A. Chem. Rev. 1996, 96, 1.
25. Reviews on sequential reactions: (a) Nakai, T.; Mikami, K. Kagaku No Ryoiki 1982, 36, 661; Chem. Abstr. 1982, 96, 16001. (b) Ziegler, F. E. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 875. (c) Ho, T.-L. Tandem Organic Reactions; Wiley: New York, 1992. (d) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131. (e) Special issue on frontiers in organic reaction sequence: Wender, P. A. Chem. Rev. 1996, 96, 1.
26. Reviews on sequential reactions: (a) Nakai, T.; Mikami, K. Kagaku No Ryoiki 1982, 36, 661; Chem. Abstr. 1982, 96, 16001. (b) Ziegler, F. E. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 875. (c) Ho, T.-L. Tandem Organic Reactions; Wiley: New York, 1992. (d) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131. (e) Special issue on frontiers in organic reaction sequence: Wender, P. A. Chem. Rev. 1996, 96, 1.
27. Reviews on sequential reactions: (a) Nakai, T.; Mikami, K. Kagaku No Ryoiki 1982, 36, 661; Chem. Abstr. 1982, 96, 16001. (b) Ziegler, F. E. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 875. (c) Ho, T.-L. Tandem Organic Reactions; Wiley: New York, 1992. (d) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131. (e) Special issue on frontiers in organic reaction sequence: Wender, P. A. Chem. Rev. 1996, 96, 1.
28. Reviews on sequential reactions: (a) Nakai, T.; Mikami, K. Kagaku No Ryoiki 1982, 36, 661; Chem. Abstr. 1982, 96, 16001. (b) Ziegler, F. E. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 875. (c) Ho, T.-L. Tandem Organic Reactions; Wiley: New York, 1992. (d) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131. (e) Special issue on frontiers in organic reaction sequence: Wender, P. A. Chem. Rev. 1996, 96, 1.
29. For recent reviews on transition metal fluorides, see (a) Murphy, E. F.; Murugavel, R.; Roesky, H. W. Chem. Rev. 1997, 97, 3425; and references therein. (b) Doherty, N. M.; Hoffman, N. W. Chem. Rev. 1991, 91, 553. (c) Pagenkopf, B. L.; Carreira, E. C. Chem.-Eur. J. 1999, 5, 3437.
30. For recent reviews on transition metal fluorides, see (a) Murphy, E. F.; Murugavel, R.; Roesky, H. W. Chem. Rev. 1997, 97, 3425; and references therein. (b) Doherty, N. M.; Hoffman, N. W. Chem. Rev. 1991, 91, 553. (c) Pagenkopf, B. L.; Carreira, E. C. Chem.-Eur. J. 1999, 5, 3437.
31. For recent reviews on transition metal fluorides, see (a) Murphy, E. F.; Murugavel, R.; Roesky, H. W. Chem. Rev. 1997, 97, 3425; and references therein. (b) Doherty, N. M.; Hoffman, N. W. Chem. Rev. 1991, 91, 553. (c) Pagenkopf, B. L.; Carreira, E. C. Chem.-Eur. J. 1999, 5, 3437.
32. Spectral data of adduct 2a and 2c were agreement with the literature data. (a) For adduct 2a see: Sambaiah, T.; Huang, D.-J.; Cheng, C.-H. J. Chem. Soc., Perkin Trans. 1 2000, 195. (b) For adduct 2c see: Crump, S. L.; Rickborn, B. J. Org. Chem. 1984, 49, 304.
33. Spectral data of adduct 2a and 2c were agreement with the literature data. (a) For adduct 2a see: Sambaiah, T.; Huang, D.-J.; Cheng, C.-H. J. Chem. Soc., Perkin Trans. 1 2000, 195. (b) For adduct 2c see: Crump, S. L.; Rickborn, B. J. Org. Chem. 1984, 49, 304.
34. 4 Complex: (a) Gauthier, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363. (b) Duthaler, R. O.; Hafner, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 43.
35. 4 Complex: (a) Gauthier, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363. (b) Duthaler, R. O.; Hafner, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 43.