| Title: | "A suite of novel allenes from Australian melolonthine scarab beetles. Structure, synthesis, and stereochemistry" |
| Author(s): | McGrath MJ; Fletcher MT; Konig WA; Moore CJ; Cribb BW; Allsopp PG; Kitching W; |
| Address: | "Department of Chemistry and Department of Zoology and Entomology, University of Queensland, Brisbane, Australia" |
| ISSN/ISBN: | 0022-3263 (Print) 0022-3263 (Linking) |
| 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 CH(3)(CH(2))(n)()CH=*=CH(CH(2))(7)CH(3) with n being 11-15, 17 and 19, and thus, all have Delta(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 (+/-)-Delta(9.10)-tricosadiene and Delta(9,10)-pentacosadiene were separable on a modified beta-cyclodextrin column (gas chromatography), and the natural Delta(9,10)-tricosadiene (n = 11) and Delta(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" |
| Keywords: | "*Alkenes/chemical synthesis/chemistry/isolation & purification Animals Australia Chromatography, Gas Coleoptera/*chemistry Indicators and Reagents Molecular Structure Nuclear Magnetic Resonance, Biomolecular Pheromones/chemistry Stereoisomerism;" |
| Notes: | "MedlineMcGrath, Matthew J Fletcher, Mary T Konig, Wilfried A Moore, Christopher J Cribb, Bronwen W Allsopp, Peter G Kitching, William eng Research Support, Non-U.S. Gov't 2003/05/10 J Org Chem. 2003 May 16; 68(10):3739-48. doi: 10.1021/jo026213j" |
