Issue 2, 2011

Asymmetric total synthesis of (+)-swainsonine

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

Supplementary files

Article information

Article type
Paper
Submitted
06 Jul 2010
Accepted
15 Sep 2010
First published
19 Oct 2010

Org. Biomol. Chem., 2011,9, 531-537

Asymmetric total synthesis of (+)-swainsonine

S. Chooprayoon, C. Kuhakarn, P. Tuchinda, V. Reutrakul and M. Pohmakotr, Org. Biomol. Chem., 2011, 9, 531 DOI: 10.1039/C0OB00388C

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