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

McGrath, M.J., Fletcher, M.T., König, W.A., Moore, C.J., Cribb, B.W., 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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