Stereoselective synthesis of (-)-swainsonine and 1,2-di-epi-swainsonine from gamma-hydroxy-alpha,beta-unsaturated sulfones

Authors
de Vicente, J Arrayas, RG Canada, J Carretero, JC
Citation
J. De Vicente et al., Stereoselective synthesis of (-)-swainsonine and 1,2-di-epi-swainsonine from gamma-hydroxy-alpha,beta-unsaturated sulfones, SYNLETT, (1), 2000, pp. 53-56
Citations number
31
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
1
Year of publication
2000
Pages
53 - 56
Database
ISI
SICI code
0936-5214(200001):1<53:SSO(A1>2.0.ZU;2-Q
Abstract
Efficient and stereodivergent syntheses of (-)-swainsonine and 1,2-di-epi-s wainsonine starting from the readily available enantiomerically pure gamma- hydroxy-alpha,beta-unsaturated sulfone (R)-2 are described. The stereoselec tivity in the osmium-dihydroxylation step of the unsaturated indolizidines 8 was highly dependent on the substitution at C8. 1,2-di-epi-swainsonine wa s found to be a good inhibitor of alpha-D-mannosidase (jack bean).