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Synthesis 2000; 2000(13): 1956-1978
DOI: 10.1055/s-2000-8232
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Synthesis and Stereochemistry of Insect Derived Spiroacetals with Branched Carbon Skeletons

Yong Q. Tu* , Achim Hübener, Hesheng Zhang, Christopher J. Moore, Mary T. Fletcher, Patricia Hayes, Konrad Dettner, Wittko Francke, Christopher S. P. McErlean, William Kitching
  • *Department of Chemistry, The University of Queensland, Brisbane, Q. 4072, Australia; Fax +61(7)33 65 42 99; E-mail: kitching@chemistry.uq.edu.au
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Publication History

Publication Date:
31 December 2000 (online)

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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.

branched spiroacetals - Cantao parentum - Ontholestes murinus - enantioselective gas chromatography - enantioselective synthesis