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Synthesis 2003(4): 0539-0544
DOI: 10.1055/s-2003-37657
PAPER
© Georg Thieme Verlag Stuttgart · New York

A [4+2] Heterocycloaddition Route to (±)-9-Decanolides

Arnaud Martela, Vincent Maisonneuveb, Eric Browna, Gilles Dujardin*a
a Laboratoire de Synthèse Organique (UMR 6011), Université du Maine, Avenue Olivier Messiaen, 72085 Le Mans Cedex 9, France
Fax: +33(2)43833366; e-Mail: Gilles.Dujardin@univ-lemans.fr;
b Laboratoire des Fluorures (UMR 6010), Université du Maine, Avenue Olivier Messiaen, 72085 Le Mans Cedex 9, France
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Publication History

Received 4 September 2002
Publication Date:
07 March 2003 (online)

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Abstract

A convergent synthetic pathway for access to the functionalized (±)-9-decanolides is described, using a [4+2] bicyclic heterocycloadduct as the key intermediate. Thus, the exo adduct (±)-10 led to the hemiacetal (±)-14a via a 4-step sequence. Free radical oxidation of (±)-14a by means of iodine and iodosobenzene diacetate under UV light gave the model 9-decanolide (±)-15 in 53% yield.

Key words

9-decanolides - bicyclic adducts - Diels-Alder reactions - radical reactions - macrocycles - lactones