Issue 22, 2009
From the journal:

Chemical Communications

The first enantioselective synthesis of palinurin†

Manuel Pérez,a   Daniel I. Pérez,‡b   Ana Martínez,‡b   Ana Castro,b   Generosa Gómez*a  and  Yagamare Fall*a  

* Corresponding authors

a Departamento de Química Orgánica, Facultad de Química, Universidad de Vigo, Spain
E-mail: yagamare@uvigo.es, ggomez@uvigo.es
Fax: +34 986 81 22 62
Tel: +34 986 81 23 20

b NOSCIRA, S.A., Avda. de la Industria 52, Spain

Abstract

The first enantioselective synthesis of palinurin has been accomplished starting from commercially available furaldehyde and (R)-methyl-3-hydroxy-2-methylpropionate; the key steps of the synthesis include the use of a chiral pyrrolidine to create the chiral tetronic moiety, and Horner–Wadsworth–Emmons, Wittig and Wittig–Horner reactions to construct the alkene units.

Graphical abstract: The first enantioselective synthesis of palinurin

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Article information

DOI
https://doi.org/10.1039/B822679B
Article type
Communication
Submitted
18 Dec 2008
Accepted
06 Apr 2009
First published
05 May 2009

Chem. Commun., 2009, 3252-3254

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The first enantioselective synthesis of palinurin

M. Pérez, D. I. Pérez, A. Martínez, A. Castro, G. Gómez and Y. Fall, Chem. Commun., 2009, 3252 DOI: 10.1039/B822679B

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