Acid-promoted rearrangement of cyclic α,β-epoxy acylates: Stereoselective synthesis of spirocyclanes and quaternary carbon centers

Journal of Organic Chemistry

Volumn 62, Issue 15, 1997, Pages 4991-4997

  Kita, Yasuyuki ^a   Kitagaki, Shinji ^a   Yoshida, Yutaka ^a   Mihara, Sachiko ^a   Fang, Dai Fei ^a   Kondo, Michinori ^a   Okamoto, Sachi ^a   Imai, Reiko ^a   Akai, Shuji ^a   Fujioka, Hiromichi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; SPIRO COMPOUND; SPIROCYCLANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 8544276578     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970035q     Document Type: Article

References (48)

1. For examples of electron-donating hydroxy derivatives initiating cleavage of the oxirane ring at the α-position of the hydroxy function and successive migration, see: Maruoka, K.; Sato, J.; Yamamoto, H. Tetrahedron 1992, 48, 3749. Nagasawa, T.; Taya, K.; Kitamura, M. Suzuki, K. J. Am. Chem. Soc. 1996, 118, 8949 and references cited therein. Rearrangement of epoxy alcohol derivative, see: Marson, C. M.; Walker, A. J.; Pickering, J.; Hobson A. D.; Wrigglesworth, R.; Edge, S. J. J. Org. Chem 1993, 58, 5944 and references cited therein.
2. For examples of electron-donating hydroxy derivatives initiating cleavage of the oxirane ring at the α-position of the hydroxy function and successive migration, see: Maruoka, K.; Sato, J.; Yamamoto, H. Tetrahedron 1992, 48, 3749. Nagasawa, T.; Taya, K.; Kitamura, M. Suzuki, K. J. Am. Chem. Soc. 1996, 118, 8949 and references cited therein. Rearrangement of epoxy alcohol derivative, see: Marson, C. M.; Walker, A. J.; Pickering, J.; Hobson A. D.; Wrigglesworth, R.; Edge, S. J. J. Org. Chem 1993, 58, 5944 and references cited therein.
3. For examples of electron-donating hydroxy derivatives initiating cleavage of the oxirane ring at the α-position of the hydroxy function and successive migration, see: Maruoka, K.; Sato, J.; Yamamoto, H. Tetrahedron 1992, 48, 3749. Nagasawa, T.; Taya, K.; Kitamura, M. Suzuki, K. J. Am. Chem. Soc. 1996, 118, 8949 and references cited therein. Rearrangement of epoxy alcohol derivative, see: Marson, C. M.; Walker, A. J.; Pickering, J.; Hobson A. D.; Wrigglesworth, R.; Edge, S. J. J. Org. Chem 1993, 58, 5944 and references cited therein.
4. For an example of epoxy acetates, see: Coxon, J. M.; Hartshorn, M. P.; Kirk, D. N. Tetrahedron 1964, 20, 2531; 1964, 20, 2547. In these cases, however, the yields of the rearranged products were very low and the regioselective cleavage of the oxirane ring was not observed.
5. For an example of epoxy acetates, see: Coxon, J. M.; Hartshorn, M. P.; Kirk, D. N. Tetrahedron 1964, 20, 2531; 1964, 20, 2547. In these cases, however, the yields of the rearranged products were very low and the regioselective cleavage of the oxirane ring was not observed.
6. Pittman, C. U., Jr.; McManus, S. P.; Larsen, J. W. Chem. Rev. 1972, 72, 357.
7. Fujioka, H.; Kitagaki, S.; Imai, R.; Kondo, M.; Okamoto, S.; Yoshida, Y.; Akai, S.; Kita, Y. Tetrahedron Lett. 1995, 36, 3219.
8. Devon, T. K.; Scott, A. I. Handbook of Naturally Occurring Compounds; Academic Press: New York, 1972; Vol. II. Marshall, J. A.; Brady, S. F.; Andersen, N. H. Fortsch Chem. Org. Naturst. 1974, 31, 283. Vandewalle, M.; De Clercq, P. Tetrahedron 1985, 41, 1767.
9. Devon, T. K.; Scott, A. I. Handbook of Naturally Occurring Compounds; Academic Press: New York, 1972; Vol. II. Marshall, J. A.; Brady, S. F.; Andersen, N. H. Fortsch Chem. Org. Naturst. 1974, 31, 283. Vandewalle, M.; De Clercq, P. Tetrahedron 1985, 41, 1767.
10. Devon, T. K.; Scott, A. I. Handbook of Naturally Occurring Compounds; Academic Press: New York, 1972; Vol. II. Marshall, J. A.; Brady, S. F.; Andersen, N. H. Fortsch Chem. Org. Naturst. 1974, 31, 283. Vandewalle, M.; De Clercq, P. Tetrahedron 1985, 41, 1767.
11. Nakadaira, Y.; Hirota, Y.; Nakanishi, K. J. Chem. Soc., Chem. Commun. 1969, 1467 and references cited therein.
12. For recent examples of spirocyclane systems, see: Tokunaga, Y.; Yagihashi, M.; Ihara, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1, 1997, 189. Knolker, H.-J.; Jones, P. G.; Graf, R. Synlett 1996, 1155. Sattelkau, T.; Hollmann, C.; Eilbracht, P. Synlett 1996, 1221. Trost, B. M.; Chen, D. W. C. J. Am. Chem. Soc. 1996, 118, 12541. Hatsui, T.; Wang, J.-J.; Ikeda, S.; Takeshita, H. Synlett 1995, 35. Patra, D.; Ghosh, S. J. Chem. Soc., Perkin Trans. 1 1995, 2635. Kuroda, C.; Hirono, Y. Tetrahedron Lett. 1994, 35, 6895. Provencal, D. P.; Leahy, J. W. J. Org. Chem. 1994, 59, 5496; Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. Jenkins, T. J.; Burnell, D. J. J. Org. Chem. 1994, 59, 1485. Mandai, T.; Tsujiguchi, Y.; Tsuji, J.; Saito, S. Tetrahedron Lett. 1994, 35, 5701. Fuchs, K.; Paquette, L. A. J. Org. Chem. 1994, 59, 528. Sands, R. D. J. Org. Chem. 1994, 59, 468. Kessar, S. V.; Vohra, R.; Kaur, N. P.; Singh, K. N.; Singh, P. J. Chem. Soc., Chem. Commun. 1994, 1327. Rao, A. V. R.; Singh, A. K.; Reddy, K. M.; Ravikumar, K. J. Chem. Soc., Perkin Trans 1 1993, 3171 and references cited therein. For reviews, see: Krapcho, A. P. Synthesis 1974, 383; 1976, 425; 1978, 77.
13. For recent examples of spirocyclane systems, see: Tokunaga, Y.; Yagihashi, M.; Ihara, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1, 1997, 189. Knolker, H.-J.; Jones, P. G.; Graf, R. Synlett 1996, 1155. Sattelkau, T.; Hollmann, C.; Eilbracht, P. Synlett 1996, 1221. Trost, B. M.; Chen, D. W. C. J. Am. Chem. Soc. 1996, 118, 12541. Hatsui, T.; Wang, J.-J.; Ikeda, S.; Takeshita, H. Synlett 1995, 35. Patra, D.; Ghosh, S. J. Chem. Soc., Perkin Trans. 1 1995, 2635. Kuroda, C.; Hirono, Y. Tetrahedron Lett. 1994, 35, 6895. Provencal, D. P.; Leahy, J. W. J. Org. Chem. 1994, 59, 5496; Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. Jenkins, T. J.; Burnell, D. J. J. Org. Chem. 1994, 59, 1485. Mandai, T.; Tsujiguchi, Y.; Tsuji, J.; Saito, S. Tetrahedron Lett. 1994, 35, 5701. Fuchs, K.; Paquette, L. A. J. Org. Chem. 1994, 59, 528. Sands, R. D. J. Org. Chem. 1994, 59, 468. Kessar, S. V.; Vohra, R.; Kaur, N. P.; Singh, K. N.; Singh, P. J. Chem. Soc., Chem. Commun. 1994, 1327. Rao, A. V. R.; Singh, A. K.; Reddy, K. M.; Ravikumar, K. J. Chem. Soc., Perkin Trans 1 1993, 3171 and references cited therein. For reviews, see: Krapcho, A. P. Synthesis 1974, 383; 1976, 425; 1978, 77.
14. For recent examples of spirocyclane systems, see: Tokunaga, Y.; Yagihashi, M.; Ihara, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1, 1997, 189. Knolker, H.-J.; Jones, P. G.; Graf, R. Synlett 1996, 1155. Sattelkau, T.; Hollmann, C.; Eilbracht, P. Synlett 1996, 1221. Trost, B. M.; Chen, D. W. C. J. Am. Chem. Soc. 1996, 118, 12541. Hatsui, T.; Wang, J.-J.; Ikeda, S.; Takeshita, H. Synlett 1995, 35. Patra, D.; Ghosh, S. J. Chem. Soc., Perkin Trans. 1 1995, 2635. Kuroda, C.; Hirono, Y. Tetrahedron Lett. 1994, 35, 6895. Provencal, D. P.; Leahy, J. W. J. Org. Chem. 1994, 59, 5496; Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. Jenkins, T. J.; Burnell, D. J. J. Org. Chem. 1994, 59, 1485. Mandai, T.; Tsujiguchi, Y.; Tsuji, J.; Saito, S. Tetrahedron Lett. 1994, 35, 5701. Fuchs, K.; Paquette, L. A. J. Org. Chem. 1994, 59, 528. Sands, R. D. J. Org. Chem. 1994, 59, 468. Kessar, S. V.; Vohra, R.; Kaur, N. P.; Singh, K. N.; Singh, P. J. Chem. Soc., Chem. Commun. 1994, 1327. Rao, A. V. R.; Singh, A. K.; Reddy, K. M.; Ravikumar, K. J. Chem. Soc., Perkin Trans 1 1993, 3171 and references cited therein. For reviews, see: Krapcho, A. P. Synthesis 1974, 383; 1976, 425; 1978, 77.
15. For recent examples of spirocyclane systems, see: Tokunaga, Y.; Yagihashi, M.; Ihara, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1, 1997, 189. Knolker, H.-J.; Jones, P. G.; Graf, R. Synlett 1996, 1155. Sattelkau, T.; Hollmann, C.; Eilbracht, P. Synlett 1996, 1221. Trost, B. M.; Chen, D. W. C. J. Am. Chem. Soc. 1996, 118, 12541. Hatsui, T.; Wang, J.-J.; Ikeda, S.; Takeshita, H. Synlett 1995, 35. Patra, D.; Ghosh, S. J. Chem. Soc., Perkin Trans. 1 1995, 2635. Kuroda, C.; Hirono, Y. Tetrahedron Lett. 1994, 35, 6895. Provencal, D. P.; Leahy, J. W. J. Org. Chem. 1994, 59, 5496; Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. Jenkins, T. J.; Burnell, D. J. J. Org. Chem. 1994, 59, 1485. Mandai, T.; Tsujiguchi, Y.; Tsuji, J.; Saito, S. Tetrahedron Lett. 1994, 35, 5701. Fuchs, K.; Paquette, L. A. J. Org. Chem. 1994, 59, 528. Sands, R. D. J. Org. Chem. 1994, 59, 468. Kessar, S. V.; Vohra, R.; Kaur, N. P.; Singh, K. N.; Singh, P. J. Chem. Soc., Chem. Commun. 1994, 1327. Rao, A. V. R.; Singh, A. K.; Reddy, K. M.; Ravikumar, K. J. Chem. Soc., Perkin Trans 1 1993, 3171 and references cited therein. For reviews, see: Krapcho, A. P. Synthesis 1974, 383; 1976, 425; 1978, 77.
16. For recent examples of spirocyclane systems, see: Tokunaga, Y.; Yagihashi, M.; Ihara, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1, 1997, 189. Knolker, H.-J.; Jones, P. G.; Graf, R. Synlett 1996, 1155. Sattelkau, T.; Hollmann, C.; Eilbracht, P. Synlett 1996, 1221. Trost, B. M.; Chen, D. W. C. J. Am. Chem. Soc. 1996, 118, 12541. Hatsui, T.; Wang, J.-J.; Ikeda, S.; Takeshita, H. Synlett 1995, 35. Patra, D.; Ghosh, S. J. Chem. Soc., Perkin Trans. 1 1995, 2635. Kuroda, C.; Hirono, Y. Tetrahedron Lett. 1994, 35, 6895. Provencal, D. P.; Leahy, J. W. J. Org. Chem. 1994, 59, 5496; Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. Jenkins, T. J.; Burnell, D. J. J. Org. Chem. 1994, 59, 1485. Mandai, T.; Tsujiguchi, Y.; Tsuji, J.; Saito, S. Tetrahedron Lett. 1994, 35, 5701. Fuchs, K.; Paquette, L. A. J. Org. Chem. 1994, 59, 528. Sands, R. D. J. Org. Chem. 1994, 59, 468. Kessar, S. V.; Vohra, R.; Kaur, N. P.; Singh, K. N.; Singh, P. J. Chem. Soc., Chem. Commun. 1994, 1327. Rao, A. V. R.; Singh, A. K.; Reddy, K. M.; Ravikumar, K. J. Chem. Soc., Perkin Trans 1 1993, 3171 and references cited therein. For reviews, see: Krapcho, A. P. Synthesis 1974, 383; 1976, 425; 1978, 77.
17. For recent examples of spirocyclane systems, see: Tokunaga, Y.; Yagihashi, M.; Ihara, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1, 1997, 189. Knolker, H.-J.; Jones, P. G.; Graf, R. Synlett 1996, 1155. Sattelkau, T.; Hollmann, C.; Eilbracht, P. Synlett 1996, 1221. Trost, B. M.; Chen, D. W. C. J. Am. Chem. Soc. 1996, 118, 12541. Hatsui, T.; Wang, J.-J.; Ikeda, S.; Takeshita, H. Synlett 1995, 35. Patra, D.; Ghosh, S. J. Chem. Soc., Perkin Trans. 1 1995, 2635. Kuroda, C.; Hirono, Y. Tetrahedron Lett. 1994, 35, 6895. Provencal, D. P.; Leahy, J. W. J. Org. Chem. 1994, 59, 5496; Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. Jenkins, T. J.; Burnell, D. J. J. Org. Chem. 1994, 59, 1485. Mandai, T.; Tsujiguchi, Y.; Tsuji, J.; Saito, S. Tetrahedron Lett. 1994, 35, 5701. Fuchs, K.; Paquette, L. A. J. Org. Chem. 1994, 59, 528. Sands, R. D. J. Org. Chem. 1994, 59, 468. Kessar, S. V.; Vohra, R.; Kaur, N. P.; Singh, K. N.; Singh, P. J. Chem. Soc., Chem. Commun. 1994, 1327. Rao, A. V. R.; Singh, A. K.; Reddy, K. M.; Ravikumar, K. J. Chem. Soc., Perkin Trans 1 1993, 3171 and references cited therein. For reviews, see: Krapcho, A. P. Synthesis 1974, 383; 1976, 425; 1978, 77.
18. For recent examples of spirocyclane systems, see: Tokunaga, Y.; Yagihashi, M.; Ihara, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1, 1997, 189. Knolker, H.-J.; Jones, P. G.; Graf, R. Synlett 1996, 1155. Sattelkau, T.; Hollmann, C.; Eilbracht, P. Synlett 1996, 1221. Trost, B. M.; Chen, D. W. C. J. Am. Chem. Soc. 1996, 118, 12541. Hatsui, T.; Wang, J.-J.; Ikeda, S.; Takeshita, H. Synlett 1995, 35. Patra, D.; Ghosh, S. J. Chem. Soc., Perkin Trans. 1 1995, 2635. Kuroda, C.; Hirono, Y. Tetrahedron Lett. 1994, 35, 6895. Provencal, D. P.; Leahy, J. W. J. Org. Chem. 1994, 59, 5496; Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. Jenkins, T. J.; Burnell, D. J. J. Org. Chem. 1994, 59, 1485. Mandai, T.; Tsujiguchi, Y.; Tsuji, J.; Saito, S. Tetrahedron Lett. 1994, 35, 5701. Fuchs, K.; Paquette, L. A. J. Org. Chem. 1994, 59, 528. Sands, R. D. J. Org. Chem. 1994, 59, 468. Kessar, S. V.; Vohra, R.; Kaur, N. P.; Singh, K. N.; Singh, P. J. Chem. Soc., Chem. Commun. 1994, 1327. Rao, A. V. R.; Singh, A. K.; Reddy, K. M.; Ravikumar, K. J. Chem. Soc., Perkin Trans 1 1993, 3171 and references cited therein. For reviews, see: Krapcho, A. P. Synthesis 1974, 383; 1976, 425; 1978, 77.
19. For recent examples of spirocyclane systems, see: Tokunaga, Y.; Yagihashi, M.; Ihara, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1, 1997, 189. Knolker, H.-J.; Jones, P. G.; Graf, R. Synlett 1996, 1155. Sattelkau, T.; Hollmann, C.; Eilbracht, P. Synlett 1996, 1221. Trost, B. M.; Chen, D. W. C. J. Am. Chem. Soc. 1996, 118, 12541. Hatsui, T.; Wang, J.-J.; Ikeda, S.; Takeshita, H. Synlett 1995, 35. Patra, D.; Ghosh, S. J. Chem. Soc., Perkin Trans. 1 1995, 2635. Kuroda, C.; Hirono, Y. Tetrahedron Lett. 1994, 35, 6895. Provencal, D. P.; Leahy, J. W. J. Org. Chem. 1994, 59, 5496; Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. Jenkins, T. J.; Burnell, D. J. J. Org. Chem. 1994, 59, 1485. Mandai, T.; Tsujiguchi, Y.; Tsuji, J.; Saito, S. Tetrahedron Lett. 1994, 35, 5701. Fuchs, K.; Paquette, L. A. J. Org. Chem. 1994, 59, 528. Sands, R. D. J. Org. Chem. 1994, 59, 468. Kessar, S. V.; Vohra, R.; Kaur, N. P.; Singh, K. N.; Singh, P. J. Chem. Soc., Chem. Commun. 1994, 1327. Rao, A. V. R.; Singh, A. K.; Reddy, K. M.; Ravikumar, K. J. Chem. Soc., Perkin Trans 1 1993, 3171 and references cited therein. For reviews, see: Krapcho, A. P. Synthesis 1974, 383; 1976, 425; 1978, 77.
20. For recent examples of spirocyclane systems, see: Tokunaga, Y.; Yagihashi, M.; Ihara, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1, 1997, 189. Knolker, H.-J.; Jones, P. G.; Graf, R. Synlett 1996, 1155. Sattelkau, T.; Hollmann, C.; Eilbracht, P. Synlett 1996, 1221. Trost, B. M.; Chen, D. W. C. J. Am. Chem. Soc. 1996, 118, 12541. Hatsui, T.; Wang, J.-J.; Ikeda, S.; Takeshita, H. Synlett 1995, 35. Patra, D.; Ghosh, S. J. Chem. Soc., Perkin Trans. 1 1995, 2635. Kuroda, C.; Hirono, Y. Tetrahedron Lett. 1994, 35, 6895. Provencal, D. P.; Leahy, J. W. J. Org. Chem. 1994, 59, 5496; Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. Jenkins, T. J.; Burnell, D. J. J. Org. Chem. 1994, 59, 1485. Mandai, T.; Tsujiguchi, Y.; Tsuji, J.; Saito, S. Tetrahedron Lett. 1994, 35, 5701. Fuchs, K.; Paquette, L. A. J. Org. Chem. 1994, 59, 528. Sands, R. D. J. Org. Chem. 1994, 59, 468. Kessar, S. V.; Vohra, R.; Kaur, N. P.; Singh, K. N.; Singh, P. J. Chem. Soc., Chem. Commun. 1994, 1327. Rao, A. V. R.; Singh, A. K.; Reddy, K. M.; Ravikumar, K. J. Chem. Soc., Perkin Trans 1 1993, 3171 and references cited therein. For reviews, see: Krapcho, A. P. Synthesis 1974, 383; 1976, 425; 1978, 77.
21. For recent examples of spirocyclane systems, see: Tokunaga, Y.; Yagihashi, M.; Ihara, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1, 1997, 189. Knolker, H.-J.; Jones, P. G.; Graf, R. Synlett 1996, 1155. Sattelkau, T.; Hollmann, C.; Eilbracht, P. Synlett 1996, 1221. Trost, B. M.; Chen, D. W. C. J. Am. Chem. Soc. 1996, 118, 12541. Hatsui, T.; Wang, J.-J.; Ikeda, S.; Takeshita, H. Synlett 1995, 35. Patra, D.; Ghosh, S. J. Chem. Soc., Perkin Trans. 1 1995, 2635. Kuroda, C.; Hirono, Y. Tetrahedron Lett. 1994, 35, 6895. Provencal, D. P.; Leahy, J. W. J. Org. Chem. 1994, 59, 5496; Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. Jenkins, T. J.; Burnell, D. J. J. Org. Chem. 1994, 59, 1485. Mandai, T.; Tsujiguchi, Y.; Tsuji, J.; Saito, S. Tetrahedron Lett. 1994, 35, 5701. Fuchs, K.; Paquette, L. A. J. Org. Chem. 1994, 59, 528. Sands, R. D. J. Org. Chem. 1994, 59, 468. Kessar, S. V.; Vohra, R.; Kaur, N. P.; Singh, K. N.; Singh, P. J. Chem. Soc., Chem. Commun. 1994, 1327. Rao, A. V. R.; Singh, A. K.; Reddy, K. M.; Ravikumar, K. J. Chem. Soc., Perkin Trans 1 1993, 3171 and references cited therein. For reviews, see: Krapcho, A. P. Synthesis 1974, 383; 1976, 425; 1978, 77.
22. For recent examples of spirocyclane systems, see: Tokunaga, Y.; Yagihashi, M.; Ihara, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1, 1997, 189. Knolker, H.-J.; Jones, P. G.; Graf, R. Synlett 1996, 1155. Sattelkau, T.; Hollmann, C.; Eilbracht, P. Synlett 1996, 1221. Trost, B. M.; Chen, D. W. C. J. Am. Chem. Soc. 1996, 118, 12541. Hatsui, T.; Wang, J.-J.; Ikeda, S.; Takeshita, H. Synlett 1995, 35. Patra, D.; Ghosh, S. J. Chem. Soc., Perkin Trans. 1 1995, 2635. Kuroda, C.; Hirono, Y. Tetrahedron Lett. 1994, 35, 6895. Provencal, D. P.; Leahy, J. W. J. Org. Chem. 1994, 59, 5496; Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. Jenkins, T. J.; Burnell, D. J. J. Org. Chem. 1994, 59, 1485. Mandai, T.; Tsujiguchi, Y.; Tsuji, J.; Saito, S. Tetrahedron Lett. 1994, 35, 5701. Fuchs, K.; Paquette, L. A. J. Org. Chem. 1994, 59, 528. Sands, R. D. J. Org. Chem. 1994, 59, 468. Kessar, S. V.; Vohra, R.; Kaur, N. P.; Singh, K. N.; Singh, P. J. Chem. Soc., Chem. Commun. 1994, 1327. Rao, A. V. R.; Singh, A. K.; Reddy, K. M.; Ravikumar, K. J. Chem. Soc., Perkin Trans 1 1993, 3171 and references cited therein. For reviews, see: Krapcho, A. P. Synthesis 1974, 383; 1976, 425; 1978, 77.
23. For recent examples of spirocyclane systems, see: Tokunaga, Y.; Yagihashi, M.; Ihara, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1, 1997, 189. Knolker, H.-J.; Jones, P. G.; Graf, R. Synlett 1996, 1155. Sattelkau, T.; Hollmann, C.; Eilbracht, P. Synlett 1996, 1221. Trost, B. M.; Chen, D. W. C. J. Am. Chem. Soc. 1996, 118, 12541. Hatsui, T.; Wang, J.-J.; Ikeda, S.; Takeshita, H. Synlett 1995, 35. Patra, D.; Ghosh, S. J. Chem. Soc., Perkin Trans. 1 1995, 2635. Kuroda, C.; Hirono, Y. Tetrahedron Lett. 1994, 35, 6895. Provencal, D. P.; Leahy, J. W. J. Org. Chem. 1994, 59, 5496; Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. Jenkins, T. J.; Burnell, D. J. J. Org. Chem. 1994, 59, 1485. Mandai, T.; Tsujiguchi, Y.; Tsuji, J.; Saito, S. Tetrahedron Lett. 1994, 35, 5701. Fuchs, K.; Paquette, L. A. J. Org. Chem. 1994, 59, 528. Sands, R. D. J. Org. Chem. 1994, 59, 468. Kessar, S. V.; Vohra, R.; Kaur, N. P.; Singh, K. N.; Singh, P. J. Chem. Soc., Chem. Commun. 1994, 1327. Rao, A. V. R.; Singh, A. K.; Reddy, K. M.; Ravikumar, K. J. Chem. Soc., Perkin Trans 1 1993, 3171 and references cited therein. For reviews, see: Krapcho, A. P. Synthesis 1974, 383; 1976, 425; 1978, 77.
24. For recent examples of spirocyclane systems, see: Tokunaga, Y.; Yagihashi, M.; Ihara, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1, 1997, 189. Knolker, H.-J.; Jones, P. G.; Graf, R. Synlett 1996, 1155. Sattelkau, T.; Hollmann, C.; Eilbracht, P. Synlett 1996, 1221. Trost, B. M.; Chen, D. W. C. J. Am. Chem. Soc. 1996, 118, 12541. Hatsui, T.; Wang, J.-J.; Ikeda, S.; Takeshita, H. Synlett 1995, 35. Patra, D.; Ghosh, S. J. Chem. Soc., Perkin Trans. 1 1995, 2635. Kuroda, C.; Hirono, Y. Tetrahedron Lett. 1994, 35, 6895. Provencal, D. P.; Leahy, J. W. J. Org. Chem. 1994, 59, 5496; Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. Jenkins, T. J.; Burnell, D. J. J. Org. Chem. 1994, 59, 1485. Mandai, T.; Tsujiguchi, Y.; Tsuji, J.; Saito, S. Tetrahedron Lett. 1994, 35, 5701. Fuchs, K.; Paquette, L. A. J. Org. Chem. 1994, 59, 528. Sands, R. D. J. Org. Chem. 1994, 59, 468. Kessar, S. V.; Vohra, R.; Kaur, N. P.; Singh, K. N.; Singh, P. J. Chem. Soc., Chem. Commun. 1994, 1327. Rao, A. V. R.; Singh, A. K.; Reddy, K. M.; Ravikumar, K. J. Chem. Soc., Perkin Trans 1 1993, 3171 and references cited therein. For reviews, see: Krapcho, A. P. Synthesis 1974, 383; 1976, 425; 1978, 77.
25. For recent examples of spirocyclane systems, see: Tokunaga, Y.; Yagihashi, M.; Ihara, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1, 1997, 189. Knolker, H.-J.; Jones, P. G.; Graf, R. Synlett 1996, 1155. Sattelkau, T.; Hollmann, C.; Eilbracht, P. Synlett 1996, 1221. Trost, B. M.; Chen, D. W. C. J. Am. Chem. Soc. 1996, 118, 12541. Hatsui, T.; Wang, J.-J.; Ikeda, S.; Takeshita, H. Synlett 1995, 35. Patra, D.; Ghosh, S. J. Chem. Soc., Perkin Trans. 1 1995, 2635. Kuroda, C.; Hirono, Y. Tetrahedron Lett. 1994, 35, 6895. Provencal, D. P.; Leahy, J. W. J. Org. Chem. 1994, 59, 5496; Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. Jenkins, T. J.; Burnell, D. J. J. Org. Chem. 1994, 59, 1485. Mandai, T.; Tsujiguchi, Y.; Tsuji, J.; Saito, S. Tetrahedron Lett. 1994, 35, 5701. Fuchs, K.; Paquette, L. A. J. Org. Chem. 1994, 59, 528. Sands, R. D. J. Org. Chem. 1994, 59, 468. Kessar, S. V.; Vohra, R.; Kaur, N. P.; Singh, K. N.; Singh, P. J. Chem. Soc., Chem. Commun. 1994, 1327. Rao, A. V. R.; Singh, A. K.; Reddy, K. M.; Ravikumar, K. J. Chem. Soc., Perkin Trans 1 1993, 3171 and references cited therein. For reviews, see: Krapcho, A. P. Synthesis 1974, 383; 1976, 425; 1978, 77.
26. For recent examples of spirocyclane systems, see: Tokunaga, Y.; Yagihashi, M.; Ihara, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1, 1997, 189. Knolker, H.-J.; Jones, P. G.; Graf, R. Synlett 1996, 1155. Sattelkau, T.; Hollmann, C.; Eilbracht, P. Synlett 1996, 1221. Trost, B. M.; Chen, D. W. C. J. Am. Chem. Soc. 1996, 118, 12541. Hatsui, T.; Wang, J.-J.; Ikeda, S.; Takeshita, H. Synlett 1995, 35. Patra, D.; Ghosh, S. J. Chem. Soc., Perkin Trans. 1 1995, 2635. Kuroda, C.; Hirono, Y. Tetrahedron Lett. 1994, 35, 6895. Provencal, D. P.; Leahy, J. W. J. Org. Chem. 1994, 59, 5496; Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. Jenkins, T. J.; Burnell, D. J. J. Org. Chem. 1994, 59, 1485. Mandai, T.; Tsujiguchi, Y.; Tsuji, J.; Saito, S. Tetrahedron Lett. 1994, 35, 5701. Fuchs, K.; Paquette, L. A. J. Org. Chem. 1994, 59, 528. Sands, R. D. J. Org. Chem. 1994, 59, 468. Kessar, S. V.; Vohra, R.; Kaur, N. P.; Singh, K. N.; Singh, P. J. Chem. Soc., Chem. Commun. 1994, 1327. Rao, A. V. R.; Singh, A. K.; Reddy, K. M.; Ravikumar, K. J. Chem. Soc., Perkin Trans 1 1993, 3171 and references cited therein. For reviews, see: Krapcho, A. P. Synthesis 1974, 383; 1976, 425; 1978, 77.
27. For recent examples of spirocyclane systems, see: Tokunaga, Y.; Yagihashi, M.; Ihara, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1, 1997, 189. Knolker, H.-J.; Jones, P. G.; Graf, R. Synlett 1996, 1155. Sattelkau, T.; Hollmann, C.; Eilbracht, P. Synlett 1996, 1221. Trost, B. M.; Chen, D. W. C. J. Am. Chem. Soc. 1996, 118, 12541. Hatsui, T.; Wang, J.-J.; Ikeda, S.; Takeshita, H. Synlett 1995, 35. Patra, D.; Ghosh, S. J. Chem. Soc., Perkin Trans. 1 1995, 2635. Kuroda, C.; Hirono, Y. Tetrahedron Lett. 1994, 35, 6895. Provencal, D. P.; Leahy, J. W. J. Org. Chem. 1994, 59, 5496; Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. Jenkins, T. J.; Burnell, D. J. J. Org. Chem. 1994, 59, 1485. Mandai, T.; Tsujiguchi, Y.; Tsuji, J.; Saito, S. Tetrahedron Lett. 1994, 35, 5701. Fuchs, K.; Paquette, L. A. J. Org. Chem. 1994, 59, 528. Sands, R. D. J. Org. Chem. 1994, 59, 468. Kessar, S. V.; Vohra, R.; Kaur, N. P.; Singh, K. N.; Singh, P. J. Chem. Soc., Chem. Commun. 1994, 1327. Rao, A. V. R.; Singh, A. K.; Reddy, K. M.; Ravikumar, K. J. Chem. Soc., Perkin Trans 1 1993, 3171 and references cited therein. For reviews, see: Krapcho, A. P. Synthesis 1974, 383; 1976, 425; 1978, 77.
28. For recent examples of spirocyclane systems, see: Tokunaga, Y.; Yagihashi, M.; Ihara, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1, 1997, 189. Knolker, H.-J.; Jones, P. G.; Graf, R. Synlett 1996, 1155. Sattelkau, T.; Hollmann, C.; Eilbracht, P. Synlett 1996, 1221. Trost, B. M.; Chen, D. W. C. J. Am. Chem. Soc. 1996, 118, 12541. Hatsui, T.; Wang, J.-J.; Ikeda, S.; Takeshita, H. Synlett 1995, 35. Patra, D.; Ghosh, S. J. Chem. Soc., Perkin Trans. 1 1995, 2635. Kuroda, C.; Hirono, Y. Tetrahedron Lett. 1994, 35, 6895. Provencal, D. P.; Leahy, J. W. J. Org. Chem. 1994, 59, 5496; Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. Jenkins, T. J.; Burnell, D. J. J. Org. Chem. 1994, 59, 1485. Mandai, T.; Tsujiguchi, Y.; Tsuji, J.; Saito, S. Tetrahedron Lett. 1994, 35, 5701. Fuchs, K.; Paquette, L. A. J. Org. Chem. 1994, 59, 528. Sands, R. D. J. Org. Chem. 1994, 59, 468. Kessar, S. V.; Vohra, R.; Kaur, N. P.; Singh, K. N.; Singh, P. J. Chem. Soc., Chem. Commun. 1994, 1327. Rao, A. V. R.; Singh, A. K.; Reddy, K. M.; Ravikumar, K. J. Chem. Soc., Perkin Trans 1 1993, 3171 and references cited therein. For reviews, see: Krapcho, A. P. Synthesis 1974, 383; 1976, 425; 1978, 77.
29. For recent examples of spirocyclane systems, see: Tokunaga, Y.; Yagihashi, M.; Ihara, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1, 1997, 189. Knolker, H.-J.; Jones, P. G.; Graf, R. Synlett 1996, 1155. Sattelkau, T.; Hollmann, C.; Eilbracht, P. Synlett 1996, 1221. Trost, B. M.; Chen, D. W. C. J. Am. Chem. Soc. 1996, 118, 12541. Hatsui, T.; Wang, J.-J.; Ikeda, S.; Takeshita, H. Synlett 1995, 35. Patra, D.; Ghosh, S. J. Chem. Soc., Perkin Trans. 1 1995, 2635. Kuroda, C.; Hirono, Y. Tetrahedron Lett. 1994, 35, 6895. Provencal, D. P.; Leahy, J. W. J. Org. Chem. 1994, 59, 5496; Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104. Jenkins, T. J.; Burnell, D. J. J. Org. Chem. 1994, 59, 1485. Mandai, T.; Tsujiguchi, Y.; Tsuji, J.; Saito, S. Tetrahedron Lett. 1994, 35, 5701. Fuchs, K.; Paquette, L. A. J. Org. Chem. 1994, 59, 528. Sands, R. D. J. Org. Chem. 1994, 59, 468. Kessar, S. V.; Vohra, R.; Kaur, N. P.; Singh, K. N.; Singh, P. J. Chem. Soc., Chem. Commun. 1994, 1327. Rao, A. V. R.; Singh, A. K.; Reddy, K. M.; Ravikumar, K. J. Chem. Soc., Perkin Trans 1 1993, 3171 and references cited therein. For reviews, see: Krapcho, A. P. Synthesis 1974, 383; 1976, 425; 1978, 77.
30. For recent examples of the asymmetric synthesis of chiral spirocyclane systems, see: Takemoto, Y.; Kuraoka, S.; Ohra, T.; Yonetoku, Y.; Iwata, C. Tetrahedron 1997, 53, 603. Zhu, Y.-Y.; Burnell, D. J. Tetrahedron: Asymmetry 1996, 7, 3295. Huang, H.; Forsyth, C. J. J. Org. Chem. 1995, 60, 2773. Villar, J. M.; Delgado, A.; Llebaria, A.; Moreto, J. M. Tetrahedron: Asymmetry 1995, 6, 665. Chitkul, B.; Pinyopronpanich, Y.; Thebtaranonth, C.; Thebtaranonth, Y.; Taylor, W. C. Tetrahedron Lett. 1994, 35, 1099. Galvez, J. M. G.; Angers, P.; Canonne, P. Tetrahedron Lett. 1994, 35, 2849. Maezaki, N.; Fukuyama, H.; Yagi, S., Tanaka, T.; Iwata, C. J. Chem. Soc., Chem. Commun. 1994, 1835. Knölker, H.-J.; Graf, R. Tetrahedron Lett. 1993, 34, 4765 and references cited therein. For review, see: Murai, A. J. Synth. Org. Chem. Jpn. 1981, 39, 893.
31. For recent examples of the asymmetric synthesis of chiral spirocyclane systems, see: Takemoto, Y.; Kuraoka, S.; Ohra, T.; Yonetoku, Y.; Iwata, C. Tetrahedron 1997, 53, 603. Zhu, Y.-Y.; Burnell, D. J. Tetrahedron: Asymmetry 1996, 7, 3295. Huang, H.; Forsyth, C. J. J. Org. Chem. 1995, 60, 2773. Villar, J. M.; Delgado, A.; Llebaria, A.; Moreto, J. M. Tetrahedron: Asymmetry 1995, 6, 665. Chitkul, B.; Pinyopronpanich, Y.; Thebtaranonth, C.; Thebtaranonth, Y.; Taylor, W. C. Tetrahedron Lett. 1994, 35, 1099. Galvez, J. M. G.; Angers, P.; Canonne, P. Tetrahedron Lett. 1994, 35, 2849. Maezaki, N.; Fukuyama, H.; Yagi, S., Tanaka, T.; Iwata, C. J. Chem. Soc., Chem. Commun. 1994, 1835. Knölker, H.-J.; Graf, R. Tetrahedron Lett. 1993, 34, 4765 and references cited therein. For review, see: Murai, A. J. Synth. Org. Chem. Jpn. 1981, 39, 893.
32. For recent examples of the asymmetric synthesis of chiral spirocyclane systems, see: Takemoto, Y.; Kuraoka, S.; Ohra, T.; Yonetoku, Y.; Iwata, C. Tetrahedron 1997, 53, 603. Zhu, Y.-Y.; Burnell, D. J. Tetrahedron: Asymmetry 1996, 7, 3295. Huang, H.; Forsyth, C. J. J. Org. Chem. 1995, 60, 2773. Villar, J. M.; Delgado, A.; Llebaria, A.; Moreto, J. M. Tetrahedron: Asymmetry 1995, 6, 665. Chitkul, B.; Pinyopronpanich, Y.; Thebtaranonth, C.; Thebtaranonth, Y.; Taylor, W. C. Tetrahedron Lett. 1994, 35, 1099. Galvez, J. M. G.; Angers, P.; Canonne, P. Tetrahedron Lett. 1994, 35, 2849. Maezaki, N.; Fukuyama, H.; Yagi, S., Tanaka, T.; Iwata, C. J. Chem. Soc., Chem. Commun. 1994, 1835. Knölker, H.-J.; Graf, R. Tetrahedron Lett. 1993, 34, 4765 and references cited therein. For review, see: Murai, A. J. Synth. Org. Chem. Jpn. 1981, 39, 893.
33. For recent examples of the asymmetric synthesis of chiral spirocyclane systems, see: Takemoto, Y.; Kuraoka, S.; Ohra, T.; Yonetoku, Y.; Iwata, C. Tetrahedron 1997, 53, 603. Zhu, Y.-Y.; Burnell, D. J. Tetrahedron: Asymmetry 1996, 7, 3295. Huang, H.; Forsyth, C. J. J. Org. Chem. 1995, 60, 2773. Villar, J. M.; Delgado, A.; Llebaria, A.; Moreto, J. M. Tetrahedron: Asymmetry 1995, 6, 665. Chitkul, B.; Pinyopronpanich, Y.; Thebtaranonth, C.; Thebtaranonth, Y.; Taylor, W. C. Tetrahedron Lett. 1994, 35, 1099. Galvez, J. M. G.; Angers, P.; Canonne, P. Tetrahedron Lett. 1994, 35, 2849. Maezaki, N.; Fukuyama, H.; Yagi, S., Tanaka, T.; Iwata, C. J. Chem. Soc., Chem. Commun. 1994, 1835. Knölker, H.-J.; Graf, R. Tetrahedron Lett. 1993, 34, 4765 and references cited therein. For review, see: Murai, A. J. Synth. Org. Chem. Jpn. 1981, 39, 893.
34. For recent examples of the asymmetric synthesis of chiral spirocyclane systems, see: Takemoto, Y.; Kuraoka, S.; Ohra, T.; Yonetoku, Y.; Iwata, C. Tetrahedron 1997, 53, 603. Zhu, Y.-Y.; Burnell, D. J. Tetrahedron: Asymmetry 1996, 7, 3295. Huang, H.; Forsyth, C. J. J. Org. Chem. 1995, 60, 2773. Villar, J. M.; Delgado, A.; Llebaria, A.; Moreto, J. M. Tetrahedron: Asymmetry 1995, 6, 665. Chitkul, B.; Pinyopronpanich, Y.; Thebtaranonth, C.; Thebtaranonth, Y.; Taylor, W. C. Tetrahedron Lett. 1994, 35, 1099. Galvez, J. M. G.; Angers, P.; Canonne, P. Tetrahedron Lett. 1994, 35, 2849. Maezaki, N.; Fukuyama, H.; Yagi, S., Tanaka, T.; Iwata, C. J. Chem. Soc., Chem. Commun. 1994, 1835. Knölker, H.-J.; Graf, R. Tetrahedron Lett. 1993, 34, 4765 and references cited therein. For review, see: Murai, A. J. Synth. Org. Chem. Jpn. 1981, 39, 893.
35. For recent examples of the asymmetric synthesis of chiral spirocyclane systems, see: Takemoto, Y.; Kuraoka, S.; Ohra, T.; Yonetoku, Y.; Iwata, C. Tetrahedron 1997, 53, 603. Zhu, Y.-Y.; Burnell, D. J. Tetrahedron: Asymmetry 1996, 7, 3295. Huang, H.; Forsyth, C. J. J. Org. Chem. 1995, 60, 2773. Villar, J. M.; Delgado, A.; Llebaria, A.; Moreto, J. M. Tetrahedron: Asymmetry 1995, 6, 665. Chitkul, B.; Pinyopronpanich, Y.; Thebtaranonth, C.; Thebtaranonth, Y.; Taylor, W. C. Tetrahedron Lett. 1994, 35, 1099. Galvez, J. M. G.; Angers, P.; Canonne, P. Tetrahedron Lett. 1994, 35, 2849. Maezaki, N.; Fukuyama, H.; Yagi, S., Tanaka, T.; Iwata, C. J. Chem. Soc., Chem. Commun. 1994, 1835. Knölker, H.-J.; Graf, R. Tetrahedron Lett. 1993, 34, 4765 and references cited therein. For review, see: Murai, A. J. Synth. Org. Chem. Jpn. 1981, 39, 893.
36. For recent examples of the asymmetric synthesis of chiral spirocyclane systems, see: Takemoto, Y.; Kuraoka, S.; Ohra, T.; Yonetoku, Y.; Iwata, C. Tetrahedron 1997, 53, 603. Zhu, Y.-Y.; Burnell, D. J. Tetrahedron: Asymmetry 1996, 7, 3295. Huang, H.; Forsyth, C. J. J. Org. Chem. 1995, 60, 2773. Villar, J. M.; Delgado, A.; Llebaria, A.; Moreto, J. M. Tetrahedron: Asymmetry 1995, 6, 665. Chitkul, B.; Pinyopronpanich, Y.; Thebtaranonth, C.; Thebtaranonth, Y.; Taylor, W. C. Tetrahedron Lett. 1994, 35, 1099. Galvez, J. M. G.; Angers, P.; Canonne, P. Tetrahedron Lett. 1994, 35, 2849. Maezaki, N.; Fukuyama, H.; Yagi, S., Tanaka, T.; Iwata, C. J. Chem. Soc., Chem. Commun. 1994, 1835. Knölker, H.-J.; Graf, R. Tetrahedron Lett. 1993, 34, 4765 and references cited therein. For review, see: Murai, A. J. Synth. Org. Chem. Jpn. 1981, 39, 893.
37. For recent examples of the asymmetric synthesis of chiral spirocyclane systems, see: Takemoto, Y.; Kuraoka, S.; Ohra, T.; Yonetoku, Y.; Iwata, C. Tetrahedron 1997, 53, 603. Zhu, Y.-Y.; Burnell, D. J. Tetrahedron: Asymmetry 1996, 7, 3295. Huang, H.; Forsyth, C. J. J. Org. Chem. 1995, 60, 2773. Villar, J. M.; Delgado, A.; Llebaria, A.; Moreto, J. M. Tetrahedron: Asymmetry 1995, 6, 665. Chitkul, B.; Pinyopronpanich, Y.; Thebtaranonth, C.; Thebtaranonth, Y.; Taylor, W. C. Tetrahedron Lett. 1994, 35, 1099. Galvez, J. M. G.; Angers, P.; Canonne, P. Tetrahedron Lett. 1994, 35, 2849. Maezaki, N.; Fukuyama, H.; Yagi, S., Tanaka, T.; Iwata, C. J. Chem. Soc., Chem. Commun. 1994, 1835. Knölker, H.-J.; Graf, R. Tetrahedron Lett. 1993, 34, 4765 and references cited therein. For review, see: Murai, A. J. Synth. Org. Chem. Jpn. 1981, 39, 893.
38. For recent examples of the asymmetric synthesis of chiral spirocyclane systems, see: Takemoto, Y.; Kuraoka, S.; Ohra, T.; Yonetoku, Y.; Iwata, C. Tetrahedron 1997, 53, 603. Zhu, Y.-Y.; Burnell, D. J. Tetrahedron: Asymmetry 1996, 7, 3295. Huang, H.; Forsyth, C. J. J. Org. Chem. 1995, 60, 2773. Villar, J. M.; Delgado, A.; Llebaria, A.; Moreto, J. M. Tetrahedron: Asymmetry 1995, 6, 665. Chitkul, B.; Pinyopronpanich, Y.; Thebtaranonth, C.; Thebtaranonth, Y.; Taylor, W. C. Tetrahedron Lett. 1994, 35, 1099. Galvez, J. M. G.; Angers, P.; Canonne, P. Tetrahedron Lett. 1994, 35, 2849. Maezaki, N.; Fukuyama, H.; Yagi, S., Tanaka, T.; Iwata, C. J. Chem. Soc., Chem. Commun. 1994, 1835. Knölker, H.-J.; Graf, R. Tetrahedron Lett. 1993, 34, 4765 and references cited therein. For review, see: Murai, A. J. Synth. Org. Chem. Jpn. 1981, 39, 893.
39. 4-reduction of the rearranged products followed by acetylation proved the presence of the 2-(acyloxy)-1-oxo moiety.
40. Ishihara, K.; Hanaki, N.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 7074.
41. For examples, see: Jung, M. E.; D'Amico, D. C. J. Am. Chem. Soc. 1995, 117, 7379. Fuji, K. Chem. Rev. 1993, 93, 2037. d'Angelo, J.; Desmaële, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459. Martin S. F. Tetrahedron 1980, 36, 419.
42. For examples, see: Jung, M. E.; D'Amico, D. C. J. Am. Chem. Soc. 1995, 117, 7379. Fuji, K. Chem. Rev. 1993, 93, 2037. d'Angelo, J.; Desmaële, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459. Martin S. F. Tetrahedron 1980, 36, 419.
43. For examples, see: Jung, M. E.; D'Amico, D. C. J. Am. Chem. Soc. 1995, 117, 7379. Fuji, K. Chem. Rev. 1993, 93, 2037. d'Angelo, J.; Desmaële, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459. Martin S. F. Tetrahedron 1980, 36, 419.
44. For examples, see: Jung, M. E.; D'Amico, D. C. J. Am. Chem. Soc. 1995, 117, 7379. Fuji, K. Chem. Rev. 1993, 93, 2037. d'Angelo, J.; Desmaële, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459. Martin S. F. Tetrahedron 1980, 36, 419.
45. Corey, E. J.; Bakshi, R. K.; Shibata, S.; Chen, C-P. Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925. Absolute configurations of (+)-27 and (-)-20 were deduced by referring to the literature.
46. Sharpless, K. B.; Michaelson, R. C. J. Am. Chem. Soc. 1973, 95, 6136.
47. Hiyama, T.; Shinoda, M.; Tsukanaka, M.; Nozaki, H. Bull. Chem. Soc. Jpn. 1980, 53, 1010.
48. Mitsunobu, O. Synthesis 1981, 1.