A suite of novel allenes from Australian melolonthine scarab beetles. Structure, synthesis, and stereochemistryView Altmetrics View AltmetricsTools 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. Full text not currently attached. Access may be available via the Publisher's website or OpenAccess link. Article Link: http://dx.doi.org/10.1021/jo026213j Publisher URL: http://pubs.acs.org/about.html AbstractA 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.
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