One-pot diastereoselective preparation of α,β-unsaturated-γ-silylated-δ-lactones: Application towards natural compounds

Article abstract of DOI:10.1055/s-2001-9700

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-lact ones 1.