A practical synthesis of (-)-swainsonine

Journal of Organic Chemistry

Volumn 61, Issue 20, 1996, Pages 7217-7221

  Pearson, William H ^a   Hembre, Erik J ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SWAINSONINE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS;

EID: 0029826558     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961101b     Document Type: Article

References (67)

1. Isolation from the fungus Rhizoctonia leguminicola: (a) Guengerich, F. P.; DiMari, S. J.; Broquist, H. P. J. Am. Chem. Soc. 1973, 95, 2055. (b) Schneider, M. J.; Ungemach, F. S.; Broquist, H. P.; Harris, T. M. Tetrahedron 1983, 39, 29-32. From the fungus Metarhizium anisopliae: (c) Hino, M.; Nakayama, O.; Tsurumi, Y.; Adachi, K.; Shibata, T.; Terano, H.; Kohsaka, M.; Aoki, H.; Imanaka, H. J. Antibiot. 1985, 35, 926-935. (d) Patrick, M. S.; Adlard, M. W.; Keshavarz, T. Biotechnol. Lett. 1995, 17, 433-438. From the legume Swainsona canescens: (e) Colegate, S. M.; Dorling, P. R.; Huxtable, C. R. Aust. J. Chem. 1979, 32, 2257-64. From the locoweed Astragalus lentiginosus: (f) Molyneux, R. J.; James, L. F. Science 1982, 216, 190-191. From Weir vine: (g) Molyneux, R. J.; McKenzie, R. A.; O'Sullivan, B. M.; Elbein, A. D. J. Nat. Prod. 1995, 58, 878-886.
2. Isolation from the fungus Rhizoctonia leguminicola: (a) Guengerich, F. P.; DiMari, S. J.; Broquist, H. P. J. Am. Chem. Soc. 1973, 95, 2055. (b) Schneider, M. J.; Ungemach, F. S.; Broquist, H. P.; Harris, T. M. Tetrahedron 1983, 39, 29-32. From the fungus Metarhizium anisopliae: (c) Hino, M.; Nakayama, O.; Tsurumi, Y.; Adachi, K.; Shibata, T.; Terano, H.; Kohsaka, M.; Aoki, H.; Imanaka, H. J. Antibiot. 1985, 35, 926-935. (d) Patrick, M. S.; Adlard, M. W.; Keshavarz, T. Biotechnol. Lett. 1995, 17, 433-438. From the legume Swainsona canescens: (e) Colegate, S. M.; Dorling, P. R.; Huxtable, C. R. Aust. J. Chem. 1979, 32, 2257-64. From the locoweed Astragalus lentiginosus: (f) Molyneux, R. J.; James, L. F. Science 1982, 216, 190-191. From Weir vine: (g) Molyneux, R. J.; McKenzie, R. A.; O'Sullivan, B. M.; Elbein, A. D. J. Nat. Prod. 1995, 58, 878-886.
3. Isolation from the fungus Rhizoctonia leguminicola: (a) Guengerich, F. P.; DiMari, S. J.; Broquist, H. P. J. Am. Chem. Soc. 1973, 95, 2055. (b) Schneider, M. J.; Ungemach, F. S.; Broquist, H. P.; Harris, T. M. Tetrahedron 1983, 39, 29-32. From the fungus Metarhizium anisopliae: (c) Hino, M.; Nakayama, O.; Tsurumi, Y.; Adachi, K.; Shibata, T.; Terano, H.; Kohsaka, M.; Aoki, H.; Imanaka, H. J. Antibiot. 1985, 35, 926-935. (d) Patrick, M. S.; Adlard, M. W.; Keshavarz, T. Biotechnol. Lett. 1995, 17, 433-438. From the legume Swainsona canescens: (e) Colegate, S. M.; Dorling, P. R.; Huxtable, C. R. Aust. J. Chem. 1979, 32, 2257-64. From the locoweed Astragalus lentiginosus: (f) Molyneux, R. J.; James, L. F. Science 1982, 216, 190-191. From Weir vine: (g) Molyneux, R. J.; McKenzie, R. A.; O'Sullivan, B. M.; Elbein, A. D. J. Nat. Prod. 1995, 58, 878-886.
4. Isolation from the fungus Rhizoctonia leguminicola: (a) Guengerich, F. P.; DiMari, S. J.; Broquist, H. P. J. Am. Chem. Soc. 1973, 95, 2055. (b) Schneider, M. J.; Ungemach, F. S.; Broquist, H. P.; Harris, T. M. Tetrahedron 1983, 39, 29-32. From the fungus Metarhizium anisopliae: (c) Hino, M.; Nakayama, O.; Tsurumi, Y.; Adachi, K.; Shibata, T.; Terano, H.; Kohsaka, M.; Aoki, H.; Imanaka, H. J. Antibiot. 1985, 35, 926-935. (d) Patrick, M. S.; Adlard, M. W.; Keshavarz, T. Biotechnol. Lett. 1995, 17, 433-438. From the legume Swainsona canescens: (e) Colegate, S. M.; Dorling, P. R.; Huxtable, C. R. Aust. J. Chem. 1979, 32, 2257-64. From the locoweed Astragalus lentiginosus: (f) Molyneux, R. J.; James, L. F. Science 1982, 216, 190-191. From Weir vine: (g) Molyneux, R. J.; McKenzie, R. A.; O'Sullivan, B. M.; Elbein, A. D. J. Nat. Prod. 1995, 58, 878-886.
5. Isolation from the fungus Rhizoctonia leguminicola: (a) Guengerich, F. P.; DiMari, S. J.; Broquist, H. P. J. Am. Chem. Soc. 1973, 95, 2055. (b) Schneider, M. J.; Ungemach, F. S.; Broquist, H. P.; Harris, T. M. Tetrahedron 1983, 39, 29-32. From the fungus Metarhizium anisopliae: (c) Hino, M.; Nakayama, O.; Tsurumi, Y.; Adachi, K.; Shibata, T.; Terano, H.; Kohsaka, M.; Aoki, H.; Imanaka, H. J. Antibiot. 1985, 35, 926-935. (d) Patrick, M. S.; Adlard, M. W.; Keshavarz, T. Biotechnol. Lett. 1995, 17, 433-438. From the legume Swainsona canescens: (e) Colegate, S. M.; Dorling, P. R.; Huxtable, C. R. Aust. J. Chem. 1979, 32, 2257-64. From the locoweed Astragalus lentiginosus: (f) Molyneux, R. J.; James, L. F. Science 1982, 216, 190-191. From Weir vine: (g) Molyneux, R. J.; McKenzie, R. A.; O'Sullivan, B. M.; Elbein, A. D. J. Nat. Prod. 1995, 58, 878-886.
6. Isolation from the fungus Rhizoctonia leguminicola: (a) Guengerich, F. P.; DiMari, S. J.; Broquist, H. P. J. Am. Chem. Soc. 1973, 95, 2055. (b) Schneider, M. J.; Ungemach, F. S.; Broquist, H. P.; Harris, T. M. Tetrahedron 1983, 39, 29-32. From the fungus Metarhizium anisopliae: (c) Hino, M.; Nakayama, O.; Tsurumi, Y.; Adachi, K.; Shibata, T.; Terano, H.; Kohsaka, M.; Aoki, H.; Imanaka, H. J. Antibiot. 1985, 35, 926-935. (d) Patrick, M. S.; Adlard, M. W.; Keshavarz, T. Biotechnol. Lett. 1995, 17, 433-438. From the legume Swainsona canescens: (e) Colegate, S. M.; Dorling, P. R.; Huxtable, C. R. Aust. J. Chem. 1979, 32, 2257-64. From the locoweed Astragalus lentiginosus: (f) Molyneux, R. J.; James, L. F. Science 1982, 216, 190-191. From Weir vine: (g) Molyneux, R. J.; McKenzie, R. A.; O'Sullivan, B. M.; Elbein, A. D. J. Nat. Prod. 1995, 58, 878-886.
7. Isolation from the fungus Rhizoctonia leguminicola: (a) Guengerich, F. P.; DiMari, S. J.; Broquist, H. P. J. Am. Chem. Soc. 1973, 95, 2055. (b) Schneider, M. J.; Ungemach, F. S.; Broquist, H. P.; Harris, T. M. Tetrahedron 1983, 39, 29-32. From the fungus Metarhizium anisopliae: (c) Hino, M.; Nakayama, O.; Tsurumi, Y.; Adachi, K.; Shibata, T.; Terano, H.; Kohsaka, M.; Aoki, H.; Imanaka, H. J. Antibiot. 1985, 35, 926-935. (d) Patrick, M. S.; Adlard, M. W.; Keshavarz, T. Biotechnol. Lett. 1995, 17, 433-438. From the legume Swainsona canescens: (e) Colegate, S. M.; Dorling, P. R.; Huxtable, C. R. Aust. J. Chem. 1979, 32, 2257-64. From the locoweed Astragalus lentiginosus: (f) Molyneux, R. J.; James, L. F. Science 1982, 216, 190-191. From Weir vine: (g) Molyneux, R. J.; McKenzie, R. A.; O'Sullivan, B. M.; Elbein, A. D. J. Nat. Prod. 1995, 58, 878-886.
8. For a review of the synthesis and biological activity of swainsonine and other glycosidase inhibitors, see: Nishimura, Y. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Eisevier: Amsterdam, 1992; Vol. 10, pp 495-583.
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13. Kaushal, G. P.; Elbein, A. D. Methods Enzymol. 1994, 230, 316-329.
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15. Das, P. C.; Roberts, J. D.; White, S. L.; Olden, K. Oncol. Res. 1995, 7, 425-433.
16. For example, Sigma Chemical Co. sells 1 mg of (-)-swainsonine isolated from Rhizoctonia leguminicola for ca. $100 (1995 catalog). Toronto Research Chemicals sells 1 mg of synthetic (-)-swainsonine for ca. $40.
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37. (u) Kang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049-5052. For a synthesis of the non-natural (+)-enantiomer of swainsonine, see:
38. (v) Oishi, T.; Iwakuma, T.; Hirama, M.; Ito, S. Synlett 1995, 404-406. Formal syntheses: (w) Gonzalez, F. B.; Barba, A. L.; Espina, M. R. Bull. Chem. Soc. Jpn. 1992, 65, 567-574. (x) Honda, T.; Hoshi, M.; Kanai, K.; Tsubuki, M. J. Chem. Soc., Perkin Trans. 1 1994, 2091-2101. (y) Angermann, J.; Homann, K.; Reissig, H.-U.; Zimmer, R. Synlett 1995, 1014-1016. (z) Zhou, W.-S.; Xie, W.-G.; Lu, Z.-H.; Pan, X.-F. Tetrahedron Lett. 1995, 36, 1291-1294. (aa) Zhou, W.-S.; Xie, W.-G.; Lu, Z.-H.; Pan, X.-F. J. Chem. Soc., Perkin Trans, 1 1995, 2599-2604.
39. (v) Oishi, T.; Iwakuma, T.; Hirama, M.; Ito, S. Synlett 1995, 404-406. Formal syntheses: (w) Gonzalez, F. B.; Barba, A. L.; Espina, M. R. Bull. Chem. Soc. Jpn. 1992, 65, 567-574. (x) Honda, T.; Hoshi, M.; Kanai, K.; Tsubuki, M. J. Chem. Soc., Perkin Trans. 1 1994, 2091-2101. (y) Angermann, J.; Homann, K.; Reissig, H.-U.; Zimmer, R. Synlett 1995, 1014-1016. (z) Zhou, W.-S.; Xie, W.-G.; Lu, Z.-H.; Pan, X.-F. Tetrahedron Lett. 1995, 36, 1291-1294. (aa) Zhou, W.-S.; Xie, W.-G.; Lu, Z.-H.; Pan, X.-F. J. Chem. Soc., Perkin Trans, 1 1995, 2599-2604.
40. (v) Oishi, T.; Iwakuma, T.; Hirama, M.; Ito, S. Synlett 1995, 404-406. Formal syntheses: (w) Gonzalez, F. B.; Barba, A. L.; Espina, M. R. Bull. Chem. Soc. Jpn. 1992, 65, 567-574. (x) Honda, T.; Hoshi, M.; Kanai, K.; Tsubuki, M. J. Chem. Soc., Perkin Trans. 1 1994, 2091-2101. (y) Angermann, J.; Homann, K.; Reissig, H.-U.; Zimmer, R. Synlett 1995, 1014-1016. (z) Zhou, W.-S.; Xie, W.-G.; Lu, Z.-H.; Pan, X.-F. Tetrahedron Lett. 1995, 36, 1291-1294. (aa) Zhou, W.-S.; Xie, W.-G.; Lu, Z.-H.; Pan, X.-F. J. Chem. Soc., Perkin Trans, 1 1995, 2599-2604.
41. (v) Oishi, T.; Iwakuma, T.; Hirama, M.; Ito, S. Synlett 1995, 404-406. Formal syntheses: (w) Gonzalez, F. B.; Barba, A. L.; Espina, M. R. Bull. Chem. Soc. Jpn. 1992, 65, 567-574. (x) Honda, T.; Hoshi, M.; Kanai, K.; Tsubuki, M. J. Chem. Soc., Perkin Trans. 1 1994, 2091-2101. (y) Angermann, J.; Homann, K.; Reissig, H.-U.; Zimmer, R. Synlett 1995, 1014-1016. (z) Zhou, W.-S.; Xie, W.-G.; Lu, Z.-H.; Pan, X.-F. Tetrahedron Lett. 1995, 36, 1291-1294. (aa) Zhou, W.-S.; Xie, W.-G.; Lu, Z.-H.; Pan, X.-F. J. Chem. Soc., Perkin Trans, 1 1995, 2599-2604.
42. (v) Oishi, T.; Iwakuma, T.; Hirama, M.; Ito, S. Synlett 1995, 404-406. Formal syntheses: (w) Gonzalez, F. B.; Barba, A. L.; Espina, M. R. Bull. Chem. Soc. Jpn. 1992, 65, 567-574. (x) Honda, T.; Hoshi, M.; Kanai, K.; Tsubuki, M. J. Chem. Soc., Perkin Trans. 1 1994, 2091-2101. (y) Angermann, J.; Homann, K.; Reissig, H.-U.; Zimmer, R. Synlett 1995, 1014-1016. (z) Zhou, W.-S.; Xie, W.-G.; Lu, Z.-H.; Pan, X.-F. Tetrahedron Lett. 1995, 36, 1291-1294. (aa) Zhou, W.-S.; Xie, W.-G.; Lu, Z.-H.; Pan, X.-F. J. Chem. Soc., Perkin Trans, 1 1995, 2599-2604.
43. (v) Oishi, T.; Iwakuma, T.; Hirama, M.; Ito, S. Synlett 1995, 404-406. Formal syntheses: (w) Gonzalez, F. B.; Barba, A. L.; Espina, M. R. Bull. Chem. Soc. Jpn. 1992, 65, 567-574. (x) Honda, T.; Hoshi, M.; Kanai, K.; Tsubuki, M. J. Chem. Soc., Perkin Trans. 1 1994, 2091-2101. (y) Angermann, J.; Homann, K.; Reissig, H.-U.; Zimmer, R. Synlett 1995, 1014-1016. (z) Zhou, W.-S.; Xie, W.-G.; Lu, Z.-H.; Pan, X.-F. Tetrahedron Lett. 1995, 36, 1291-1294. (aa) Zhou, W.-S.; Xie, W.-G.; Lu, Z.-H.; Pan, X.-F. J. Chem. Soc., Perkin Trans, 1 1995, 2599-2604.
44. Slaframine: (a) Pearson, W. H.; Bergmeier, S. C. J. Org. Chem. 1991, 56, 1976-1978. (b) Pearson, W. H.; Bergmeier, S, C.; Williams, J. P. J. Org. Chem. 1992, 57, 3977-3987. Australine and alexine stereoisomers: (c) Pearson, W. H.; Hines, J. V. Tetrahedron Lett. 1991, 32, 5513-5516. Ring-expanded analogs of swainsonine: (d) Pearson, W. H.; Hembre, E. J. Tetrahedron Lett. 1993, 34, 8221-8224. (e) Pearson, W. H.; Hembre, E. J. J. Org. Chem., 1996, 61, 5537-5545. Ring-expanded analogs of australine and alexine: (f) Pearson, W. H.; Hembre, E. J. J. Org. Chem., 1996, 61, 5546-5556.
45. Slaframine: (a) Pearson, W. H.; Bergmeier, S. C. J. Org. Chem. 1991, 56, 1976-1978. (b) Pearson, W. H.; Bergmeier, S, C.; Williams, J. P. J. Org. Chem. 1992, 57, 3977-3987. Australine and alexine stereoisomers: (c) Pearson, W. H.; Hines, J. V. Tetrahedron Lett. 1991, 32, 5513-5516. Ring-expanded analogs of swainsonine: (d) Pearson, W. H.; Hembre, E. J. Tetrahedron Lett. 1993, 34, 8221-8224. (e) Pearson, W. H.; Hembre, E. J. J. Org. Chem., 1996, 61, 5537-5545. Ring-expanded analogs of australine and alexine: (f) Pearson, W. H.; Hembre, E. J. J. Org. Chem., 1996, 61, 5546-5556.
46. Slaframine: (a) Pearson, W. H.; Bergmeier, S. C. J. Org. Chem. 1991, 56, 1976-1978. (b) Pearson, W. H.; Bergmeier, S, C.; Williams, J. P. J. Org. Chem. 1992, 57, 3977-3987. Australine and alexine stereoisomers: (c) Pearson, W. H.; Hines, J. V. Tetrahedron Lett. 1991, 32, 5513-5516. Ring-expanded analogs of swainsonine: (d) Pearson, W. H.; Hembre, E. J. Tetrahedron Lett. 1993, 34, 8221-8224. (e) Pearson, W. H.; Hembre, E. J. J. Org. Chem., 1996, 61, 5537-5545. Ring-expanded analogs of australine and alexine: (f) Pearson, W. H.; Hembre, E. J. J. Org. Chem., 1996, 61, 5546-5556.
47. Slaframine: (a) Pearson, W. H.; Bergmeier, S. C. J. Org. Chem. 1991, 56, 1976-1978. (b) Pearson, W. H.; Bergmeier, S, C.; Williams, J. P. J. Org. Chem. 1992, 57, 3977-3987. Australine and alexine stereoisomers: (c) Pearson, W. H.; Hines, J. V. Tetrahedron Lett. 1991, 32, 5513-5516. Ring-expanded analogs of swainsonine: (d) Pearson, W. H.; Hembre, E. J. Tetrahedron Lett. 1993, 34, 8221-8224. (e) Pearson, W. H.; Hembre, E. J. J. Org. Chem., 1996, 61, 5537-5545. Ring-expanded analogs of australine and alexine: (f) Pearson, W. H.; Hembre, E. J. J. Org. Chem., 1996, 61, 5546-5556.
48. Slaframine: (a) Pearson, W. H.; Bergmeier, S. C. J. Org. Chem. 1991, 56, 1976-1978. (b) Pearson, W. H.; Bergmeier, S, C.; Williams, J. P. J. Org. Chem. 1992, 57, 3977-3987. Australine and alexine stereoisomers: (c) Pearson, W. H.; Hines, J. V. Tetrahedron Lett. 1991, 32, 5513-5516. Ring-expanded analogs of swainsonine: (d) Pearson, W. H.; Hembre, E. J. Tetrahedron Lett. 1993, 34, 8221-8224. (e) Pearson, W. H.; Hembre, E. J. J. Org. Chem., 1996, 61, 5537-5545. Ring-expanded analogs of australine and alexine: (f) Pearson, W. H.; Hembre, E. J. J. Org. Chem., 1996, 61, 5546-5556.
49. Slaframine: (a) Pearson, W. H.; Bergmeier, S. C. J. Org. Chem. 1991, 56, 1976-1978. (b) Pearson, W. H.; Bergmeier, S, C.; Williams, J. P. J. Org. Chem. 1992, 57, 3977-3987. Australine and alexine stereoisomers: (c) Pearson, W. H.; Hines, J. V. Tetrahedron Lett. 1991, 32, 5513-5516. Ring-expanded analogs of swainsonine: (d) Pearson, W. H.; Hembre, E. J. Tetrahedron Lett. 1993, 34, 8221-8224. (e) Pearson, W. H.; Hembre, E. J. J. Org. Chem., 1996, 61, 5537-5545. Ring-expanded analogs of australine and alexine: (f) Pearson, W. H.; Hembre, E. J. J. Org. Chem., 1996, 61, 5546-5556.
50. For related one-pot double cyclizations using azido epoxides or amino epoxides, see references 11h, m and: (a) Kim, Y. G.; Cha, J. K. Tetrahedron Lett. 1989, 30, 5721-5724. (b) Ina, H.; Kibayashi, C. J. Org. Chem. 1993, 58, 52-61. (c) Jirousek, M. R.; Cheung, A. W.-H.; Babine, R. E.; Sass, P. M.; Schow, S. R.; Wick, M. M. Tetrahedron Lett. 1993, 34, 3671-3674. (d) Kim, N.-S.; Choi, J.-R.; Cha, J. K. J. Org. Chem. 1993, 58, 7096-7099. (e) Poitout, L.; Le Merrer, Y.; Depezay, J.-C. Tetrahedron Lett. 1994, 35, 3293-3296. (f) Lohray, B. B.; Jayamma, Y.; Chatterjee, M. J. Org. Chem. 1995, 60, 5958-5960.
51. For related one-pot double cyclizations using azido epoxides or amino epoxides, see references 11h, m and: (a) Kim, Y. G.; Cha, J. K. Tetrahedron Lett. 1989, 30, 5721-5724. (b) Ina, H.; Kibayashi, C. J. Org. Chem. 1993, 58, 52-61. (c) Jirousek, M. R.; Cheung, A. W.-H.; Babine, R. E.; Sass, P. M.; Schow, S. R.; Wick, M. M. Tetrahedron Lett. 1993, 34, 3671-3674. (d) Kim, N.-S.; Choi, J.-R.; Cha, J. K. J. Org. Chem. 1993, 58, 7096-7099. (e) Poitout, L.; Le Merrer, Y.; Depezay, J.-C. Tetrahedron Lett. 1994, 35, 3293-3296. (f) Lohray, B. B.; Jayamma, Y.; Chatterjee, M. J. Org. Chem. 1995, 60, 5958-5960.
52. For related one-pot double cyclizations using azido epoxides or amino epoxides, see references 11h, m and: (a) Kim, Y. G.; Cha, J. K. Tetrahedron Lett. 1989, 30, 5721-5724. (b) Ina, H.; Kibayashi, C. J. Org. Chem. 1993, 58, 52-61. (c) Jirousek, M. R.; Cheung, A. W.-H.; Babine, R. E.; Sass, P. M.; Schow, S. R.; Wick, M. M. Tetrahedron Lett. 1993, 34, 3671-3674. (d) Kim, N.-S.; Choi, J.-R.; Cha, J. K. J. Org. Chem. 1993, 58, 7096-7099. (e) Poitout, L.; Le Merrer, Y.; Depezay, J.-C. Tetrahedron Lett. 1994, 35, 3293-3296. (f) Lohray, B. B.; Jayamma, Y.; Chatterjee, M. J. Org. Chem. 1995, 60, 5958-5960.
53. For related one-pot double cyclizations using azido epoxides or amino epoxides, see references 11h, m and: (a) Kim, Y. G.; Cha, J. K. Tetrahedron Lett. 1989, 30, 5721-5724. (b) Ina, H.; Kibayashi, C. J. Org. Chem. 1993, 58, 52-61. (c) Jirousek, M. R.; Cheung, A. W.-H.; Babine, R. E.; Sass, P. M.; Schow, S. R.; Wick, M. M. Tetrahedron Lett. 1993, 34, 3671-3674. (d) Kim, N.-S.; Choi, J.-R.; Cha, J. K. J. Org. Chem. 1993, 58, 7096-7099. (e) Poitout, L.; Le Merrer, Y.; Depezay, J.-C. Tetrahedron Lett. 1994, 35, 3293-3296. (f) Lohray, B. B.; Jayamma, Y.; Chatterjee, M. J. Org. Chem. 1995, 60, 5958-5960.
54. For related one-pot double cyclizations using azido epoxides or amino epoxides, see references 11h, m and: (a) Kim, Y. G.; Cha, J. K. Tetrahedron Lett. 1989, 30, 5721-5724. (b) Ina, H.; Kibayashi, C. J. Org. Chem. 1993, 58, 52-61. (c) Jirousek, M. R.; Cheung, A. W.-H.; Babine, R. E.; Sass, P. M.; Schow, S. R.; Wick, M. M. Tetrahedron Lett. 1993, 34, 3671-3674. (d) Kim, N.-S.; Choi, J.-R.; Cha, J. K. J. Org. Chem. 1993, 58, 7096-7099. (e) Poitout, L.; Le Merrer, Y.; Depezay, J.-C. Tetrahedron Lett. 1994, 35, 3293-3296. (f) Lohray, B. B.; Jayamma, Y.; Chatterjee, M. J. Org. Chem. 1995, 60, 5958-5960.
55. For related one-pot double cyclizations using azido epoxides or amino epoxides, see references 11h, m and: (a) Kim, Y. G.; Cha, J. K. Tetrahedron Lett. 1989, 30, 5721-5724. (b) Ina, H.; Kibayashi, C. J. Org. Chem. 1993, 58, 52-61. (c) Jirousek, M. R.; Cheung, A. W.-H.; Babine, R. E.; Sass, P. M.; Schow, S. R.; Wick, M. M. Tetrahedron Lett. 1993, 34, 3671-3674. (d) Kim, N.-S.; Choi, J.-R.; Cha, J. K. J. Org. Chem. 1993, 58, 7096-7099. (e) Poitout, L.; Le Merrer, Y.; Depezay, J.-C. Tetrahedron Lett. 1994, 35, 3293-3296. (f) Lohray, B. B.; Jayamma, Y.; Chatterjee, M. J. Org. Chem. 1995, 60, 5958-5960.
56. Cohen, N.; Banner, B. L.; Laurenzano, A. J.; Carozza, L. In Organic Syntheses; Freeman, J. P., Ed.; Wiley: New York, 1990; Coll. Vol. IV, pp 297-301.
57. Dunigan, J.; Weigel, L. O. J. Org. Chem. 1991, 56, 6225-6227.
58. Cohen, N.; Banner, B. L.; Lopresti, R. J.; Wong, F.; Rosenberger, M.; Liu, Y. Y.; Thom, E.; Liebman, A. A. J. Am. Chem. Soc 1983, 105, 3661-3672.
59. Mekki, B.; Singh, G.; Wightman, R. H. Tetrahedron Lett. 1991, 32, 5143-5146.
60. Johnson, W. S.; Werthemann, L.; Bartlett, W. R.; Brocksom, T. J.; Li, T.; Faulkner, D. J.; Petersen, M. R. J. Am. Chem. Soc. 1970, 92, 741-743.
61. Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem 1992, 57, 2768-2771.
62. For similar oxidative lactonizations, see: (a) Wang, Z.-M.; Zhang, X.-L.; Sharpless, K. B. Tetrahedron Lett. 1992, 33, 6407-6410. (b) Keinan, E.; Sinha, S. C.; Sinha-Bagchi, A.; Wang, Z.-M.; Zhang, X.-L.; Sharpless, K. B. Tetrahedron Lett. 1992, 33, 6411-6414.
63. For similar oxidative lactonizations, see: (a) Wang, Z.-M.; Zhang, X.-L.; Sharpless, K. B. Tetrahedron Lett. 1992, 33, 6407-6410. (b) Keinan, E.; Sinha, S. C.; Sinha-Bagchi, A.; Wang, Z.-M.; Zhang, X.-L.; Sharpless, K. B. Tetrahedron Lett. 1992, 33, 6411-6414.
64. Alternatively, Cha's method might be used to transform 4 into swainsonine. Cha and co-workers made a compound similar to 4 (ethyl ester, Z-alkene, free hydroxy instead of (tert-butyldimethylsilyl)oxy) by a Wittig route.
65. 11m their procedure involves isolation of the borane complex of 10. Our procedure is adapted from a similar one by Keck which was used to make an epimer of swainsonine: Keck, G. E.; Romer, D. R. J. Org. Chem. 1993, 58, 6083-6089.
66. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem 1978, 43, 2923-2925.
67. 17 we have chosen to include these details herein.