Issue 39, 2013
From the journal:

Organic & Biomolecular Chemistry

Diastereoselective synthesis of the C14–C29 fragment of amphidinol 3†

Nicolas Rival,a   Gilles Hanquet,*a   Charlelie Bensoussan,b   Sébastien Reymond,b   Janine Cossyb  and  Françoise Colobert*a  

* Corresponding authors

a Laboratoire de Synthese et Catalyse Asymetrique, Université de Strasbourg (ECPM), UMR CNRS 7509, 25 Rue Becquerel, Strasbourg Cedex 02, France
E-mail: ghanquet@unistra.fr, francoise.colobert@unistra.fr
Tel: +03 68 85 27 46

b Laboratoire de Chimie Organique, ESPCI ParisTech, UMR CNRS 7084, 10 rue Vauquelin, Paris Cedex 05, France

Abstract

An efficient stereoselective synthesis of the C14–C29 fragment highlighting a coupling reaction between a 1,3-dithiane derivative and an α-branched aldehyde was realized. This highly convergent synthesis involved two chiral pools, L-malic acid and (+)-camphorsulfonic acid, which are the starting compounds to control the six stereogenic centers present in the C14–C29 fragment of amphidinol 3.

Graphical abstract: Diastereoselective synthesis of the C14–C29 fragment of amphidinol 3

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Article information

DOI
https://doi.org/10.1039/C3OB41569D
Article type
Paper
Submitted
31 Jul 2013
Accepted
15 Aug 2013
First published
15 Aug 2013

Org. Biomol. Chem., 2013,11, 6829-6840

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Diastereoselective synthesis of the C14–C29 fragment of amphidinol 3

N. Rival, G. Hanquet, C. Bensoussan, S. Reymond, J. Cossy and F. Colobert, Org. Biomol. Chem., 2013, 11, 6829 DOI: 10.1039/C3OB41569D

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