The β-Lactone Route to β-Hydroxy or α,β-Unsaturated γ- and δ-Lactones. Syntheses of (±)-Massoialactone and (±)-Prelactone B

Lycia Fournier; Anouk Gaudel-Siri; Philip J. Kocieňski; Jean-Marc Pons

doi:10.1055/s-2003-36222

LETTER

The β-Lactone Route to β-Hydroxy or α,β-Unsaturated γ- and δ-Lactones. Syntheses of (±)-Massoialactone and (±)-Prelactone B

Lycia Fournier^a, Anouk Gaudel-Siri^a, Philip J. Kocieňski^b, Jean-Marc Pons*^a
^a Laboratoire de Réactivité en Synthèse Organique (RéSO), UMR CNRS 6516, Faculté des Sciences de St-Jérôme, boîte D12, 13397 Marseille Cedex 20, France
Fax: +33(4)91288841; e-Mail: jean-marc.pons@univ.u-3mrs.fr;
^b Department of Chemistry, Leeds University, Leeds, LS29JT, UK

Abstract

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Abstract

Aqueous HF promotes the translactonization of silyloxy β-lactones into β-hydroxy or α,β-unsaturated γ- and δ-lactones. The reaction is studied from a theoretical point of view and applied to the racemic synthesis of two natural bioactive δ-lactones.

Key words

silylketene - lactone - transition state - HF - translactonization.

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References

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