476171-67-2Relevant academic research and scientific papers
Asymmetric synthesis of (-)-swainsonine
Lindsay, Karl B.,Pyne, Stephen G.
, p. 669 - 672 (2007/10/03)
This paper describes a new synthesis of (-)-swainsonine via the ring-closing metathesis reaction of a substituted 3-allyl-4-vinyloxazolindin-2- one and subsequent diastereoselective syn-dihydroxylation of the resulting pyrrolo[1,2-c]oxazol-3-one.
Asymmetric synthesis of (-)-swainsonine, (+)-1,2-di-epi-swainsonine, and (+)-1,2,8-tri-epi-swainsonine
Lindsay, Karl B.,Pyne, Stephen G.
, p. 7774 - 7780 (2007/10/03)
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-α. This synthetic strategy also allowed for the diastereoselective synthesis of (+)-1,2-di-epi-swainsonine and (+)-1,2,8-tri-epi-swainsonine.
