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Synthesis and stereochemistry of insect derived spiroacetals with branched carbon skeletons

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Tu, Y. Q., Hübener, A., Zhang, H., Moore, C. J., Fletcher, M. T., Hayes, P., Dettner, K., Francke, W., McErlean, C.S.P. and Kitching, W. (2000) Synthesis and stereochemistry of insect derived spiroacetals with branched carbon skeletons. Synthesis (13). pp. 1956-1978. ISSN 0039-7881

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Article Link: htpps://doi.org/10.1055/s-2000-8232

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.

Item Type:Article
Subjects:Science > Entomology
Live Archive:08 Jan 2024 01:48
Last Modified:08 Jan 2024 01:48

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