The First Stereoselective Synthesis of a Dithiane Derivative of the C₁₈ β-Diketodiene System Proposed for an Active Compound Isolated from Cantharellus cibarius (Chanterelle)

Abstract

A stereocontrolled synthesis of a thioketal system that is a direct precursor of an active compound isolated from chanterelle was accomplished by using readily available methyl 11-[2-(2-oxoethyl)-1,3-dithian-2-yl]undec-9-ynoate as a key intermediate. The synthesis involves simple and straightforward reactions, such as addition of a lithiated alkyne to an aldehyde, alkyne hydrogenation using nickel boride, alcohol oxidation with Dess–Martin periodinane, and Z-to-E enone isomerization.

Key words

total synthesis - stereoselective synthesis - hydroacylations - cross-coupling - organometallic reagents - thioketals

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