SYNTHESIS OF NOVEL POLYHYDROXYLATED QUINOLIZIDINES - RING EXPANDED ANALOGS OF GLYCOSIDASE INHIBITORY INDOLIZIDINES

Authors
PEARSON WH HEMBRE EJ
Citation
Wh. Pearson et Ej. Hembre, SYNTHESIS OF NOVEL POLYHYDROXYLATED QUINOLIZIDINES - RING EXPANDED ANALOGS OF GLYCOSIDASE INHIBITORY INDOLIZIDINES, Tetrahedron letters, 34(51), 1993, pp. 8221-8224
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
51
Year of publication
1993
Pages
8221 - 8224
Database
ISI
SICI code
0040-4039(1993)34:51<8221:SONPQ->2.0.ZU;2-4
Abstract
Two polyhydroxylated quinolizidines, 1R,2R,3R,9S,9aR)-1,2,3,9-tetrahyd roxyquinolizidine 9 and 1R,2R,3R,9R,9aS)-1,2,3,9-tetrahydroxyquinolizi dine 10, have been synthesized by the reductive double cyclization of 15 alpha and 15 beta. Quinolizidine 9 can be viewed either as a ring e xpanded analog of 6-epicastanospermine or of 8-episwainsonine, while 1 0 is a ring expanded analog of 1,6,8a-triepicastanospermine or of 8a-e piswainsonine.