ChemInform Abstract: A Synthesis of (.+‐.)‐Lavandulol Using a Silyl‐to‐Hydroxy Conversion in the Presence of 1,1‐Disubstituted and Trisubstituted Double Bonds.

Abstract

A Synthesis of (±)-Lavandulol Using a Silyl-to-Hydroxy Conversion in the Presence of 1,1-Disubstituted and Trisubstituted Double Bonds.-The presence of TmsCl in the addition reaction of silylcuprates and silylzincates to α,β-unsaturated aldehydes, esters, ketones and amides unsubstituted at the β-position affords higher yields of silylated products such as (X), and in most cases the silylzincates are superior to silylcuprates. This method is applied to the synthesis of lavandulol (VII) using the cuprate derived from silane (IX). The substitution of the methylbutenyl group at the silicon by fluoride is possible under mild enough conditions that do not attack the allyl double bond. For the synthesis of the silyl chloride precursor of (IX) an improved method is given. -(FLEMING, I.; LEE, D.; J.