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A suite of novel allenes from Australian melolonthine scarab beetles. Structure, synthesis, and stereochemistry

McGrath, M.J. and Fletcher, M.T. and König, W.A. and Moore, C.J. and Cribb, B.W. and Allsopp, R.G. and Kitching, W. (2003) A suite of novel allenes from Australian melolonthine scarab beetles. Structure, synthesis, and stereochemistry. Journal of Organic Chemistry, 68 (10). pp. 3739-3748.

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Article Link(s): http://dx.doi.org/10.1021/jo026213j

Publisher URL: http://pubs.acs.org/about.html

Abstract

A suite of allenic hydrocarbons, previously unknown as a molecular class from insects, has been characterized from several Australian melolonthine scarab beetles. The allenes are represented by the formula CH3(CH2)nCH==CH(CH2)7CH3 with n being 11-15, 17 and 19, and thus, all have 9,10-unsaturation. These structures have been confirmed by syntheses and comparisons of spectral and chromatographic properties with those of the natural components. The enantiomers of (±)-9.10-tricosadiene and 9,10-pentacosadiene were separable on a modified -cyclodextrin column (gas chromatography), and the natural 9,10-tricosadiene (n = 11) and 9,10-pentacosadiene (n = 13) were shown to be of >85% ee.

Syntheses of nonracemic allenes of known predominating chirality were acquired using both organotin chemistry and sulfonylhydrazine intermediates, and comparisons then demonstrated that the natural allenes were predominantly (R)-configured.

Item Type:Article
Corporate Creators:Biosecurity Queensland
Additional Information:© American Chemical Society.
Keywords:Melolonthine; scarab beetles; allenes; chirality.
Subjects:Science > Biology > Biochemistry
Science > Zoology > Invertebrates > Insects
Deposited On:07 May 2004
Last Modified:15 Jun 2011 07:02

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