Synthesis of substituted cis-decalins as potential insect antifeedants

Abstract

2β-Acetoxy-1α-acetoxymethyl-5,5-dimethyl-1α,6α,10Oα-bicyclo[4.4.0]decane-10-spiro-2′-oxiran (4) has been prepared from 4,4-dimethylcyclohex-2-enone in eight steps, one of which involves a useful Lewis acid-catalysed cyclisation of an acetylenic β-oxo-ester (7). The structure of (4) was determined by X-ray crystallography. At a concentration of 1 000 p.p.m. compound (4) showed a 72% inhibition of feeding by Locusta migratoria.