Synthesis of the Four Stereoisomers of 7-Acetoxy-15-methylnonacosane, a Component of the Female Sex Pheromone of the Screwworm Fly,Cochliomyia hominivorax | Zendy

Kenji Mori | Zendy; Takashi Ohtaki | Zendy; Hiroshi Ohrui | Zendy; Dennis R. Berkebile | Zendy; David A. Carlson | Zendy

Open Access

Synthesis of the Four Stereoisomers of 7-Acetoxy-15-methylnonacosane, a Component of the Female Sex Pheromone of the Screwworm Fly,Cochliomyia hominivorax

Author(s) -

Kenji Mori,

Takashi Ohtaki,

Hiroshi Ohrui,

Dennis R. Berkebile,

David A. Carlson

Publication year - 2004

Publication title -

bioscience biotechnology and biochemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.509

H-Index - 116

eISSN - 1347-6947

pISSN - 0916-8451

DOI - 10.1271/bbb.68.1768

Subject(s) - cochliomyia hominivorax , enantiomer , stereochemistry , pheromone , stereocenter , sex pheromone , calliphoridae , component (thermodynamics) , biology , chemistry , zoology , enantioselective synthesis , botany , biochemistry , catalysis , physics , thermodynamics , larva

The four stereoisomers of 7-acetoxy-15-methylnonacosane (1), a component of the female sex pheromone of the New World screwworm fly (Cochliomyia hominivorax) were synthesized. The stereogenic center at C-15 of 1 originated from that of the enantiomers of citronellal, and that at C-7 was generated by lipase-catalyzed asymmetric acetylation of (3RS,11R)- and (3RS,11S)-17-methyl-1-trimethylsilylpentacos-1-yn-3-ol (13). Three of the stereoisomers of 1 showed equivalent good pheromone activity, while the activity of (7R,15R)-1 was weak.

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