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Synlett 2001; 2001(1): 0138-0140
DOI: 10.1055/s-2001-9700
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One-Pot Diastereoselective Preparation of α,β-Unsaturated-γ-Silylated-δ-Lactones: Application towards Natural Compounds

Frédéric Marion* , Rachel Le Fol, Christine Courillon, Max Malacria
  • *Université P. et M. Curie, Laboratoire de Chimie Organique de Synthèse, associé au CNRS, Tour 44-54, B. 229, 04 place Jussieu, 75252 Paris Cedex 05, France; Fax 33-1-44-27-73-60; E-mail: malacria@ccr.jussieu.fr
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Publication Date:
31 December 2001 (online)

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Rearrangement of silylated vinyloxiranes into highly functionalized α-silylated-β,γ-unsaturated aldehydes occurs with total chirality transfer and retention of double bond configuration under Pd(0) catalysis. We show that this reaction is a versatile tool in the field of total stereoselective synthesis: enantiomerically pure lactones are obtained. The pheromone 6-n-undecyltetrahydro-2-pyrone 2 and massoilactone, 5-hydroxy-2-decenoic acid lactone 3, are synthesized. We describe herein a novel highly diastereoselective route to α,β-unsaturated-γ-silylated-δ-substituted-δ-lactones 1.

assymetric synthesis - lactones - natural products - palladium