Synthesis of tetrahydroxyquinolizidines: Ring-expanded analogs of the mannosidase inhibitor swainsonine

Journal of Organic Chemistry

Volumn 61, Issue 16, 1996, Pages 5537-5545

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

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME INHIBITOR; MANNOSIDASE INHIBITOR; QUINOLIZIDINE DERIVATIVE; SWAINSONINE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENZYME INHIBITION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029784236     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960609b     Document Type: Article

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46. For related one-pot double cyclizations using amino epoxides, see: (a) Setoi, H.; Takeno, H.; Hashimoto, M. J. Org. Chem. 1985, 50, 3948. (b) Setoi, H.; Takeno, H.; Hashimoto, M. Tetrahedron Lett. 1985, 26, 4617. (c) Kim, Y. G.; Cha, J. K. Tetrahedron Lett. 1989, 30, 5721. (d) Kim, N.-S.; Choi, J.-R.; Cha, J. K. J. Org. Chem 1993, 58, 7096. (e) Lohray, B. B.; Jayamma, Y.; Chatterjee, M. J. Org. Chem 1995, 60, 5958. See also: (f) Poitout, L.; Le Merrer, Y.; Depezay, J.-C. Tetrahedron Lett. 1994, 35, 3293. For one-pot double cyclizations using amines with other electrophiles, see: (g) Ina, H.; Kibayashi, C. J. Org. Chem. 1993, 58, 52. (h) Jirousek, M. R.; Cheung, A. W.-H.; Babine, R. E.; Sass, P. M.; Schow, S. R.; Wick, M. M. Tetrahedron Lett. 1993, 34, 3671.
47. For related one-pot double cyclizations using amino epoxides, see: (a) Setoi, H.; Takeno, H.; Hashimoto, M. J. Org. Chem. 1985, 50, 3948. (b) Setoi, H.; Takeno, H.; Hashimoto, M. Tetrahedron Lett. 1985, 26, 4617. (c) Kim, Y. G.; Cha, J. K. Tetrahedron Lett. 1989, 30, 5721. (d) Kim, N.-S.; Choi, J.-R.; Cha, J. K. J. Org. Chem 1993, 58, 7096. (e) Lohray, B. B.; Jayamma, Y.; Chatterjee, M. J. Org. Chem 1995, 60, 5958. See also: (f) Poitout, L.; Le Merrer, Y.; Depezay, J.-C. Tetrahedron Lett. 1994, 35, 3293. For one-pot double cyclizations using amines with other electrophiles, see: (g) Ina, H.; Kibayashi, C. J. Org. Chem. 1993, 58, 52. (h) Jirousek, M. R.; Cheung, A. W.-H.; Babine, R. E.; Sass, P. M.; Schow, S. R.; Wick, M. M. Tetrahedron Lett. 1993, 34, 3671.
48. For related one-pot double cyclizations using amino epoxides, see: (a) Setoi, H.; Takeno, H.; Hashimoto, M. J. Org. Chem. 1985, 50, 3948. (b) Setoi, H.; Takeno, H.; Hashimoto, M. Tetrahedron Lett. 1985, 26, 4617. (c) Kim, Y. G.; Cha, J. K. Tetrahedron Lett. 1989, 30, 5721. (d) Kim, N.-S.; Choi, J.-R.; Cha, J. K. J. Org. Chem 1993, 58, 7096. (e) Lohray, B. B.; Jayamma, Y.; Chatterjee, M. J. Org. Chem 1995, 60, 5958. See also: (f) Poitout, L.; Le Merrer, Y.; Depezay, J.-C. Tetrahedron Lett. 1994, 35, 3293. For one-pot double cyclizations using amines with other electrophiles, see: (g) Ina, H.; Kibayashi, C. J. Org. Chem. 1993, 58, 52. (h) Jirousek, M. R.; Cheung, A. W.-H.; Babine, R. E.; Sass, P. M.; Schow, S. R.; Wick, M. M. Tetrahedron Lett. 1993, 34, 3671.
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51. For reports of similar epoxidations of allylic ethers, see: (a) Wang, Z.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 31. (b) Erickson, S. D.; Still, W. C. Tetrahedron Lett. 1990, 31, 4253. (c) Coutts, S. J.; Wittman, M. D.; Kallmerten, J. Tetrahedron Lett. 1990, 31, 4301.
52. For reports of similar epoxidations of allylic ethers, see: (a) Wang, Z.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 31. (b) Erickson, S. D.; Still, W. C. Tetrahedron Lett. 1990, 31, 4253. (c) Coutts, S. J.; Wittman, M. D.; Kallmerten, J. Tetrahedron Lett. 1990, 31, 4301.
53. For reports of similar epoxidations of allylic ethers, see: (a) Wang, Z.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 31. (b) Erickson, S. D.; Still, W. C. Tetrahedron Lett. 1990, 31, 4253. (c) Coutts, S. J.; Wittman, M. D.; Kallmerten, J. Tetrahedron Lett. 1990, 31, 4301.
54. Attempted Jacobsen asymmetric epoxidation of 13 led to recovered starting material (Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801). Attempts to synthesize 13 with a free allylic hydroxyl group were made in order to attempt a Sharpless epoxidation, but the sequence became too cumbersome to be practical.
55. We were able to prepare a related trans alkene, ethyl (E)-(6R,7S,8R)-9-azido-6,7,8-tris(benzyloxy)non-4-enoate, using an entirely different synthesis. Epoxidatitm gave a 2:1 ratio of epoxides. The major epoxide was transformed into (9S,9aS)-4, but this route offered no significant advantage over the route shown in Scheme 6.
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58. We thank Prof. Alan D. Elbein (University of Arkansas) for the results of screening against the glucosidase I and II and mannosidase I.
59. The results of anti-HIV and anticancer testing were provided by the National Cancer Institute Developmental Therapeutics Program. Only (9S,9aR)-4 and (9A,9aS)-4 were tested in these screens.
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