Synthesis and Stereochemistry of Insect Derived Spiroacetals with Branched Carbon Skeletons

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Abstract
About thirty constitutionally different spiroacetals have been characterised from insects but only three have branched carbon skeletons. Two are based on the 1,7-dioxoaspiro[5.5]undecane system and are certain stereoisomers of the 2,4,8-trimethyl derivative, from the aposematic shield bug, Cantao parentum (White), and a 2,2,8-trimethyl derivative from the rove beetle, Ontholestes murinus (L.). The 1,6-dioxaspiro[4.5]decane system is represented by a stereoisomer of the 2,3,7-trimethyl derivative in the Cantao species. The elucidation of their structures and stereochemistry by spectroscopy, synthesis and enantioselective gas chromatography is described.

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