Issue 10, 2011
From the journal:

Organic & Biomolecular Chemistry

Synthesis of the gymnodimine tetrahydrofuran core through a Ueno–Stork radical cyclization†‡

Sylvestre Toumieux,a   Redouane Beniazza,a   Valérie Desvergnes,a   Rómulo Aráoz,b   Jordi Molgób  and  Yannick Landais*a  

* Corresponding authors

a Université de Bordeaux, Institut des Sciences Moléculaires, UMR-CNRS 5255, 351, Cours de la Libération, France
E-mail: y.landais@ism.u-bordeaux1.fr
Fax: +33 05 4000 6286
Tel: +33 05 4000 2289

b CNRS, Institut Fédératif de Neurobiologie Alfred Fessard FRC2118, Laboratoire de Neurobiologie et Développement, UPR 3294, 1 Avenue de la Terrasse, bâtiments 32-33, France

Abstract

A straightforward access to the C10–C20 skeleton of gymnodimine, incorporating a tetrahydrofuran fragment, is described. The elaboration of the THF moiety is based on a stereocontrolled Ueno–Stork cyclization. A Lewis-acid mediated allylation of the resulting acetal at C13 and a Horner–Wadsworth–Emmons olefination on the ketone at C17 complete the synthesis.

Graphical abstract: Synthesis of the gymnodimine tetrahydrofuran core through a Ueno–Stork radical cyclization

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C1OB05240C
Article type
Paper
Submitted
15 Feb 2011
Accepted
11 Mar 2011
First published
11 Mar 2011

Org. Biomol. Chem., 2011,9, 3726-3732

Permissions

Request permissions

Synthesis of the gymnodimine tetrahydrofuran core through a Ueno–Stork radical cyclization

S. Toumieux, R. Beniazza, V. Desvergnes, R. Aráoz, J. Molgó and Y. Landais, Org. Biomol. Chem., 2011, 9, 3726 DOI: 10.1039/C1OB05240C

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements