Issue 31, 2010
From the journal:

Chemical Communications

Diastereoselective formal total synthesis of (±)-triptolidevia a novel cationic cyclization of 2-alkenyl-1,3-dithiolane†

Sylvie Goncalves,a   Paul Hellier,b   Marc Nicolas,b   Alain Wagnera  and  Rachid Baati*a  

* Corresponding authors

a University of Strasbourg, Faculty of Pharmacy, Laboratory of Functional ChemoSystems CNRS/UMR 7199, 74 route du Rhin BP60024, 67400 Illkirch, France
E-mail: baati@bioorga.u-strasbg.fr
Fax: +33-368-854-306
Tel: +33-368-854-301

b Les Laboratoires Pierre Fabre Centre de Développement Chimique Industriel, 16 rue Jean Rostand, 81600 Gaillac, France

Abstract

A concise and diastereoselective formal total synthesis of triptolide, a natural product with a wide range of biological properties, is described. The key reaction is an unprecedented 6-endo-Trig cationic cyclization of a 2-alkenyl-1,3-dithiolane precursor induced by TMSOTf as Lewis acid.

Graphical abstract: Diastereoselective formal total synthesis of (±)-triptolide via a novel cationic cyclization of 2-alkenyl-1,3-dithiolane

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Article information

DOI
https://doi.org/10.1039/C0CC00250J
Article type
Communication
Submitted
05 Mar 2010
Accepted
09 Jun 2010
First published
05 Jul 2010

Chem. Commun., 2010,46, 5778-5780

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Diastereoselective formal total synthesis of (±)-triptolide via a novel cationic cyclization of 2-alkenyl-1,3-dithiolane

S. Goncalves, P. Hellier, M. Nicolas, A. Wagner and R. Baati, Chem. Commun., 2010, 46, 5778 DOI: 10.1039/C0CC00250J

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