Asymmetric synthesis of (-)-swainsonine, (+)-1,2-di-epi-swainsonine, and (+)-1,2,8-tri-epi-swainsonine.
The asymmetric synthesis of (-)-swainsonine via a nonchiral pool route that involves the Sharpless epoxidation to induce chirality is reported. The key steps involve vinyl epoxide aminolysis, ring-closing metathesis, and intramolecular N-alkylation to prepare the indolizidine ring and a highly diastereoselective cis-dihydroxylation using AD-mix-alpha. This synthetic strategy also allowed for the diastereoselective synthesis of (+)-1,2-di-epi-swainsonine and (+)-1,2,8-tri-epi-swainsonine.
Lindsay
Karl B
KB
Department of Chemistry, University of Wollongong, New South Wales 2522, Australia.
Pyne
Stephen G
SG
D000478:Alkylation; D006900:Hydroxylation; D015394:Molecular Structure; D013237:Stereoisomerism; D017026:Swainsonine / Q000138:chemical synthesis* / Q000737:chemistry*
D017026:Swainsonine