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Synthesis 2011(24): 4037-4044  
DOI: 10.1055/s-0031-1289588
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Desymmetrization of Hepta-1,6-dien-4-ol by Prins Reaction and Subsequent Cross-Metathesis: Access to Diospongine A Homologues

Ludovic Raffier, Frédéric Izquierdo, Olivier Piva*
Université de Lyon - Université Lyon 1, Institut de Chimie et de Biochimie Moléculaire et Supramoléculaire (ICBMS), UMR 5246 CNRS, Equipe SURCOOF, Bat Raulin-43, Bd du 11 novembre 1918, 69622 Villeurbanne cedex, France
Fax: +33(4)72448136; e-Mail: piva@univ-lyon1.fr;
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Publication History

Received 28 September 2011
Publication Date:
04 November 2011 (online)

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Abstract

A new tetrahydropyran scaffold has been efficiently prepared by Prins reaction between hepta-1,6-dien-4-ol and benzaldehyde. Subsequent functionalizations were further achieved by Mitsunobu reaction and/or by the way of cross-metathesis/Wacker oxidation sequence to deliver diospongin A analogues.

Key words

pyrans - Prins reaction - metathesis - Wacker oxidation - natural product

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