Asymmetric total synthesis of (+)-swainsonine?

Organic & Biomolecular Chemistry Pub Date: 2010-10-19 DOI: 10.1039/C0OB00388C

Abstract

A concise asymmetric synthesis of (+)-swainsonine (ent-1) is described starting from 2, which was readily prepared from commercially available L-glutamic acid. The method features installation of the indolizidine ring via an intramolecular cyclisation of α-sulfinyl carbanion as a key step. (+)-Swainsonine was obtained in 11.8% overall yield in 10 steps.

Graphical abstract: Asymmetric total synthesis of (+)-swainsonine
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