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
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.
|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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