Asymmetric synthesis of (-)-swainsonine, (+)-1,2-di-epi-swainsonine, and (+)-1,2,8-tri-epi-swainsonine

Journal of Organic Chemistry

Volumn 67, Issue 22, 2002, Pages 7774-7780

  Lindsay, Karl B ^a   Pyne, Stephen G ^a  

^a UNIVERSITY OF WOLLONGONG   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

DIASTEREOSELECTIVITY; EPOXIDATION; METATHESIS;

ALKYLATION; HYDROXYLATION; OXIDATION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

1,2 DIEPISWAINSONINE; 1,2,8 TRIEPISWAINSONINE; INDOLIZINE DERIVATIVE; SWAINSONINE; SWAINSONINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; EPOXIDATION; RING CLOSING METATHESIS; STEREOCHEMISTRY;

ALKYLATION; HYDROXYLATION; MOLECULAR STRUCTURE; STEREOISOMERISM; SWAINSONINE;

EID: 0036828072     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo025977w     Document Type: Article

References (59)

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13. For the application of the ring-closing metathesis reaction to the synthesis of aza-sugars, see: (a) Huwe, C. M.; Blechert, S. Tetrahedron Lett. 1995, 36, 1621-1624. (b) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547-550. (c) Huwe, C. M.; Blechert, S. Synthesis 1997, 61-67. (d) White, J. D.; Hrnciar, P.; Yokochi, A. F. T. J. Am. Chem. Soc. 1998, 120, 7359-7360. (e) Lindstrom, U. M.; Somfai, P. Tetrahedron Lett. 1998, 39, 7173-7176. (f) Ovaa, H.; Stragies, R.; van der Marcel, G. A.; van Boom, J. H.; Blechert, S. Chem. Commun. 2000, 1501-1502. (g) Subramanian, T.; Lin, C.-C.; Lin, C.-C. Tetrahedron Lett. 2001, 42, 4079-4082. (h) Klitze, C. F.; Pilli, R. A. Tetrahedron Lett. 2001, 42, 5605-5608. (i) Chandra, K. L.; Chandrasekhar, M.; Singh, V. K. J. Org. Chem. 2002, 67, 4630-4633.
14. For the application of the ring-closing metathesis reaction to the synthesis of aza-sugars, see: (a) Huwe, C. M.; Blechert, S. Tetrahedron Lett. 1995, 36, 1621-1624. (b) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547-550. (c) Huwe, C. M.; Blechert, S. Synthesis 1997, 61-67. (d) White, J. D.; Hrnciar, P.; Yokochi, A. F. T. J. Am. Chem. Soc. 1998, 120, 7359-7360. (e) Lindstrom, U. M.; Somfai, P. Tetrahedron Lett. 1998, 39, 7173-7176. (f) Ovaa, H.; Stragies, R.; van der Marcel, G. A.; van Boom, J. H.; Blechert, S. Chem. Commun. 2000, 1501-1502. (g) Subramanian, T.; Lin, C.-C.; Lin, C.-C. Tetrahedron Lett. 2001, 42, 4079-4082. (h) Klitze, C. F.; Pilli, R. A. Tetrahedron Lett. 2001, 42, 5605-5608. (i) Chandra, K. L.; Chandrasekhar, M.; Singh, V. K. J. Org. Chem. 2002, 67, 4630-4633.
15. For the application of the ring-closing metathesis reaction to the synthesis of aza-sugars, see: (a) Huwe, C. M.; Blechert, S. Tetrahedron Lett. 1995, 36, 1621-1624. (b) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547-550. (c) Huwe, C. M.; Blechert, S. Synthesis 1997, 61-67. (d) White, J. D.; Hrnciar, P.; Yokochi, A. F. T. J. Am. Chem. Soc. 1998, 120, 7359-7360. (e) Lindstrom, U. M.; Somfai, P. Tetrahedron Lett. 1998, 39, 7173-7176. (f) Ovaa, H.; Stragies, R.; van der Marcel, G. A.; van Boom, J. H.; Blechert, S. Chem. Commun. 2000, 1501-1502. (g) Subramanian, T.; Lin, C.-C.; Lin, C.-C. Tetrahedron Lett. 2001, 42, 4079-4082. (h) Klitze, C. F.; Pilli, R. A. Tetrahedron Lett. 2001, 42, 5605-5608. (i) Chandra, K. L.; Chandrasekhar, M.; Singh, V. K. J. Org. Chem. 2002, 67, 4630-4633.
16. For the application of the ring-closing metathesis reaction to the synthesis of aza-sugars, see: (a) Huwe, C. M.; Blechert, S. Tetrahedron Lett. 1995, 36, 1621-1624. (b) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547-550. (c) Huwe, C. M.; Blechert, S. Synthesis 1997, 61-67. (d) White, J. D.; Hrnciar, P.; Yokochi, A. F. T. J. Am. Chem. Soc. 1998, 120, 7359-7360. (e) Lindstrom, U. M.; Somfai, P. Tetrahedron Lett. 1998, 39, 7173-7176. (f) Ovaa, H.; Stragies, R.; van der Marcel, G. A.; van Boom, J. H.; Blechert, S. Chem. Commun. 2000, 1501-1502. (g) Subramanian, T.; Lin, C.-C.; Lin, C.-C. Tetrahedron Lett. 2001, 42, 4079-4082. (h) Klitze, C. F.; Pilli, R. A. Tetrahedron Lett. 2001, 42, 5605-5608. (i) Chandra, K. L.; Chandrasekhar, M.; Singh, V. K. J. Org. Chem. 2002, 67, 4630-4633.
17. For the application of the ring-closing metathesis reaction to the synthesis of aza-sugars, see: (a) Huwe, C. M.; Blechert, S. Tetrahedron Lett. 1995, 36, 1621-1624. (b) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547-550. (c) Huwe, C. M.; Blechert, S. Synthesis 1997, 61-67. (d) White, J. D.; Hrnciar, P.; Yokochi, A. F. T. J. Am. Chem. Soc. 1998, 120, 7359-7360. (e) Lindstrom, U. M.; Somfai, P. Tetrahedron Lett. 1998, 39, 7173-7176. (f) Ovaa, H.; Stragies, R.; van der Marcel, G. A.; van Boom, J. H.; Blechert, S. Chem. Commun. 2000, 1501-1502. (g) Subramanian, T.; Lin, C.-C.; Lin, C.-C. Tetrahedron Lett. 2001, 42, 4079-4082. (h) Klitze, C. F.; Pilli, R. A. Tetrahedron Lett. 2001, 42, 5605-5608. (i) Chandra, K. L.; Chandrasekhar, M.; Singh, V. K. J. Org. Chem. 2002, 67, 4630-4633.
18. For the application of the ring-closing metathesis reaction to the synthesis of aza-sugars, see: (a) Huwe, C. M.; Blechert, S. Tetrahedron Lett. 1995, 36, 1621-1624. (b) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547-550. (c) Huwe, C. M.; Blechert, S. Synthesis 1997, 61-67. (d) White, J. D.; Hrnciar, P.; Yokochi, A. F. T. J. Am. Chem. Soc. 1998, 120, 7359-7360. (e) Lindstrom, U. M.; Somfai, P. Tetrahedron Lett. 1998, 39, 7173-7176. (f) Ovaa, H.; Stragies, R.; van der Marcel, G. A.; van Boom, J. H.; Blechert, S. Chem. Commun. 2000, 1501-1502. (g) Subramanian, T.; Lin, C.-C.; Lin, C.-C. Tetrahedron Lett. 2001, 42, 4079-4082. (h) Klitze, C. F.; Pilli, R. A. Tetrahedron Lett. 2001, 42, 5605-5608. (i) Chandra, K. L.; Chandrasekhar, M.; Singh, V. K. J. Org. Chem. 2002, 67, 4630-4633.
19. For the application of the ring-closing metathesis reaction to the synthesis of 2,5-dihydropyrroles from dienes, see: (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376-2378. (b) Furstner, A.; Fursterner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1998, 1315-1316. (c) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869-14884. (d) Furstner, A.; Ackermann, L. Chem. Commun. 1999, 95-96. (e) Bujard, M.; Briot, A.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8795-8788. (f) Furstner, A.; Liebl, M.; Hill, A. F.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601-602. (g) Ackermann, L.; Furstner, A.; Weskamp, T.; Kohl, F. J.; Hermann, W. A. Tetrhedron Lett. 1999, 40, 4787-4790. (h) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657-8662. (i) Evans, P. A.; Robinson, J. E. Org. Lett. 1999, 1, 1929-1931. (j) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771-1772.
20. For the application of the ring-closing metathesis reaction to the synthesis of 2,5-dihydropyrroles from dienes, see: (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376-2378. (b) Furstner, A.; Fursterner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1998, 1315-1316. (c) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869-14884. (d) Furstner, A.; Ackermann, L. Chem. Commun. 1999, 95-96. (e) Bujard, M.; Briot, A.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8795-8788. (f) Furstner, A.; Liebl, M.; Hill, A. F.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601-602. (g) Ackermann, L.; Furstner, A.; Weskamp, T.; Kohl, F. J.; Hermann, W. A. Tetrhedron Lett. 1999, 40, 4787-4790. (h) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657-8662. (i) Evans, P. A.; Robinson, J. E. Org. Lett. 1999, 1, 1929-1931. (j) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771-1772.
21. For the application of the ring-closing metathesis reaction to the synthesis of 2,5-dihydropyrroles from dienes, see: (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376-2378. (b) Furstner, A.; Fursterner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1998, 1315-1316. (c) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869-14884. (d) Furstner, A.; Ackermann, L. Chem. Commun. 1999, 95-96. (e) Bujard, M.; Briot, A.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8795-8788. (f) Furstner, A.; Liebl, M.; Hill, A. F.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601-602. (g) Ackermann, L.; Furstner, A.; Weskamp, T.; Kohl, F. J.; Hermann, W. A. Tetrhedron Lett. 1999, 40, 4787-4790. (h) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657-8662. (i) Evans, P. A.; Robinson, J. E. Org. Lett. 1999, 1, 1929-1931. (j) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771-1772.
22. For the application of the ring-closing metathesis reaction to the synthesis of 2,5-dihydropyrroles from dienes, see: (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376-2378. (b) Furstner, A.; Fursterner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1998, 1315-1316. (c) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869-14884. (d) Furstner, A.; Ackermann, L. Chem. Commun. 1999, 95-96. (e) Bujard, M.; Briot, A.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8795-8788. (f) Furstner, A.; Liebl, M.; Hill, A. F.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601-602. (g) Ackermann, L.; Furstner, A.; Weskamp, T.; Kohl, F. J.; Hermann, W. A. Tetrhedron Lett. 1999, 40, 4787-4790. (h) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657-8662. (i) Evans, P. A.; Robinson, J. E. Org. Lett. 1999, 1, 1929-1931. (j) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771-1772.
23. For the application of the ring-closing metathesis reaction to the synthesis of 2,5-dihydropyrroles from dienes, see: (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376-2378. (b) Furstner, A.; Fursterner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1998, 1315-1316. (c) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869-14884. (d) Furstner, A.; Ackermann, L. Chem. Commun. 1999, 95-96. (e) Bujard, M.; Briot, A.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8795-8788. (f) Furstner, A.; Liebl, M.; Hill, A. F.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601-602. (g) Ackermann, L.; Furstner, A.; Weskamp, T.; Kohl, F. J.; Hermann, W. A. Tetrhedron Lett. 1999, 40, 4787-4790. (h) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657-8662. (i) Evans, P. A.; Robinson, J. E. Org. Lett. 1999, 1, 1929-1931. (j) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771-1772.
24. For the application of the ring-closing metathesis reaction to the synthesis of 2,5-dihydropyrroles from dienes, see: (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376-2378. (b) Furstner, A.; Fursterner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1998, 1315-1316. (c) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869-14884. (d) Furstner, A.; Ackermann, L. Chem. Commun. 1999, 95-96. (e) Bujard, M.; Briot, A.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8795-8788. (f) Furstner, A.; Liebl, M.; Hill, A. F.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601-602. (g) Ackermann, L.; Furstner, A.; Weskamp, T.; Kohl, F. J.; Hermann, W. A. Tetrhedron Lett. 1999, 40, 4787-4790. (h) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657-8662. (i) Evans, P. A.; Robinson, J. E. Org. Lett. 1999, 1, 1929-1931. (j) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771-1772.
25. For the application of the ring-closing metathesis reaction to the synthesis of 2,5-dihydropyrroles from dienes, see: (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376-2378. (b) Furstner, A.; Fursterner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1998, 1315-1316. (c) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869-14884. (d) Furstner, A.; Ackermann, L. Chem. Commun. 1999, 95-96. (e) Bujard, M.; Briot, A.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8795-8788. (f) Furstner, A.; Liebl, M.; Hill, A. F.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601-602. (g) Ackermann, L.; Furstner, A.; Weskamp, T.; Kohl, F. J.; Hermann, W. A. Tetrhedron Lett. 1999, 40, 4787-4790. (h) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657-8662. (i) Evans, P. A.; Robinson, J. E. Org. Lett. 1999, 1, 1929-1931. (j) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771-1772.
26. For the application of the ring-closing metathesis reaction to the synthesis of 2,5-dihydropyrroles from dienes, see: (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376-2378. (b) Furstner, A.; Fursterner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1998, 1315-1316. (c) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869-14884. (d) Furstner, A.; Ackermann, L. Chem. Commun. 1999, 95-96. (e) Bujard, M.; Briot, A.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8795-8788. (f) Furstner, A.; Liebl, M.; Hill, A. F.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601-602. (g) Ackermann, L.; Furstner, A.; Weskamp, T.; Kohl, F. J.; Hermann, W. A. Tetrhedron Lett. 1999, 40, 4787-4790. (h) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657-8662. (i) Evans, P. A.; Robinson, J. E. Org. Lett. 1999, 1, 1929-1931. (j) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771-1772.
27. For the application of the ring-closing metathesis reaction to the synthesis of 2,5-dihydropyrroles from dienes, see: (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376-2378. (b) Furstner, A.; Fursterner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1998, 1315-1316. (c) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869-14884. (d) Furstner, A.; Ackermann, L. Chem. Commun. 1999, 95-96. (e) Bujard, M.; Briot, A.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8795-8788. (f) Furstner, A.; Liebl, M.; Hill, A. F.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601-602. (g) Ackermann, L.; Furstner, A.; Weskamp, T.; Kohl, F. J.; Hermann, W. A. Tetrhedron Lett. 1999, 40, 4787-4790. (h) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657-8662. (i) Evans, P. A.; Robinson, J. E. Org. Lett. 1999, 1, 1929-1931. (j) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771-1772.
28. For the application of the ring-closing metathesis reaction to the synthesis of 2,5-dihydropyrroles from dienes, see: (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376-2378. (b) Furstner, A.; Fursterner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1998, 1315-1316. (c) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869-14884. (d) Furstner, A.; Ackermann, L. Chem. Commun. 1999, 95-96. (e) Bujard, M.; Briot, A.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8795-8788. (f) Furstner, A.; Liebl, M.; Hill, A. F.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601-602. (g) Ackermann, L.; Furstner, A.; Weskamp, T.; Kohl, F. J.; Hermann, W. A. Tetrhedron Lett. 1999, 40, 4787-4790. (h) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657-8662. (i) Evans, P. A.; Robinson, J. E. Org. Lett. 1999, 1, 1929-1931. (j) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771-1772.
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