Synthesis of the Enantiomers of 21-Methyl-7-hentriacontanone and a Stereoisomeric Mixture of 5-Acetoxy-19-methylnonacosane, Candidates for the Female Sex Pheromone of the Screwworm Fly…
- 1 January 2003
- journal article
- Published by Oxford University Press (OUP) in Bioscience, Biotechnology, and Biochemistry
- Vol. 67 (10) , 2224-2231
- https://doi.org/10.1271/bbb.67.2224
Abstract
The enantiomers of 21-methyl-7-hentriacontanone (1), which might show weak bioactivity as the female sex pheromone of the screwworm fly (Cochliomyia hominivorax), were synthesized by starting from the enantiomers of citronellal. (+/-)-Citronellol was converted to a racemic and diastereomeric mixture of 5-acetoxy-19-methylnonacosane (2), which was considered to be a candidate for the female sex pheromone of C. hominivorax. Synthetic 2 exhibited no pheromone activity against male C. hominivorax.Keywords
This publication has 5 references indexed in Scilit:
- Determination of the Absolute Configuration at the Two Cyclopropane Moieties of Plakoside A, an Immunosuppressive Marine GalactosphingolipidEuropean Journal of Organic Chemistry, 2002
- Syntheses of Four Methyl-branched Secondary Acetates and a Methyl-branched Ketone as Possible Candidates for the Female Pheromone of the Screwworm Fly,Cochliomyia hominivoraxBioscience, Biotechnology, and Biochemistry, 2002
- A solution of the“intrinsic problem”of diastereomer method in chiral discriminationProceedings of the Japan Academy, Series B, 2002
- Identification of compounds in an HPLC fraction from female extracts that elicit mating responses in male screwworm flies,Cochliomyia hominivoraxJournal of Chemical Ecology, 1993
- Improved Carbon‐Carbon Linking by Controlled Copper CatalysisAngewandte Chemie International Edition in English, 1974