Asymmetric synthesis of (-)-swainsonine, (+)-1,2-di-epi-swainsonine,and (+)-1,2,8-tri-epi-swainsonine |
| |
Authors: | Lindsay Karl B Pyne Stephen G |
| |
Institution: | Department of Chemistry, University of Wollongong, New South Wales 2522, Australia. |
| |
Abstract: | 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. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|