Issue 8, 2008
From the journal:

Organic & Biomolecular Chemistry

Enantioselective total synthesis of pyrinodemin A†‡

Annie Pouilhès,a   Anel Florès Amado,a   Anne Vidal,a   Yves Langloisa  and  Cyrille Kouklovsky*a  

* Corresponding authors

a Laboratoire de Chimie des Procédés et Substances Naturelles, Institut de Chimie Moléculaire et des Matériaux d′Orsay (UMR CNRS no 8182), Bâtiment 410, Univ. Paris-Sud 11, F-91405 Orsay, France
E-mail: cykouklo@icmo.u-psud.fr
Fax: +33 1 69 15 46 79
Tel: +33 1 69 15 73 91

Abstract

Pyrinodemin A 1, a cytotoxic marine alkaloid, was synthesized in a convergent and enantioselective fashion. The key steps are an asymmetric intramolecular dipolar cycloaddition of an oxazoline N-oxide to introduce the bicyclic ring system of the molecule, a cuprate coupling for the extension of the saturated chain and a B-alkyl Suzuki coupling for the introduction of a 3-pyridyl moiety. Reductive amination allowed the coupling of the second side-chain onto the nitrogen atom to give 1. Additionally, attempts to prepare 1 from a trienic precursor by a double B-alkyl Suzuki reaction are described.

Graphical abstract: Enantioselective total synthesis of pyrinodemin A

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Article information

DOI
https://doi.org/10.1039/B800840J
Article type
Paper
Submitted
17 Jan 2008
Accepted
15 Feb 2008
First published
10 Mar 2008

Org. Biomol. Chem., 2008,6, 1502-1510

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Enantioselective total synthesis of pyrinodemin A

A. Pouilhès, A. F. Amado, A. Vidal, Y. Langlois and C. Kouklovsky, Org. Biomol. Chem., 2008, 6, 1502 DOI: 10.1039/B800840J

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