Synthesis and stereochemistry of insect derived spiroacetals with branched carbon skeletons

Tu, Yong Q., Hubener, Achim, Zhang, Hesheng, Moore, Christopher J., Fletcher, Mary T., Hayes, Patricia, Dettner, Konrad, Francke, Wittko, McErlean, Christopher S. P. and Kitching, William (2000) Synthesis and stereochemistry of insect derived spiroacetals with branched carbon skeletons. Synthesis, 2000 13: 1956-1978.


Author Tu, Yong Q.
Hubener, Achim
Zhang, Hesheng
Moore, Christopher J.
Fletcher, Mary T.
Hayes, Patricia
Dettner, Konrad
Francke, Wittko
McErlean, Christopher S. P.
Kitching, William
Title Synthesis and stereochemistry of insect derived spiroacetals with branched carbon skeletons
Journal name Synthesis   Check publisher's open access policy
ISSN 0039-7881
1437-210X
Publication date 2000-11
Sub-type Article (original research)
Volume 2000
Issue 13
Start page 1956
End page 1978
Total pages 23
Place of publication Stuttgart, Germany
Publisher Georg Thieme
Language eng
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-dioxaspiro[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.
Keyword Branched spiroacetals
Cantao parentum
Ontholestes murinus
Enantioselective gas chromatography
Enantioselective synthesis
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Unknown

Document type: Journal Article
Sub-type: Article (original research)
Collections: Queensland Alliance for Agriculture and Food Innovation
School of Chemistry and Molecular Biosciences
 
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Created: Mon, 07 Mar 2011, 15:02:24 EST