Download PDF
Synthesis 2000; 2000(1): 113-118
DOI: 10.1055/s-2000-6227
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Preparative Scale Syntheses of Isomerically Pure (10E,12E,14Z)- and (10E,12E,14E)-Hexadeca-10,12,14-trienals, Sex Pheromone Components of Manduca sexta

Xin Chen* , Jocelyn G. Millar
  • *Department of Entomology, University of California, Riverside, CA 92521, USA; Fax 1 (9 09) 7 87 30 86; E-mail: jocelyn.millar@ucr.edu
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

Short, efficient syntheses yielding products of very high isomeric purity have been developed for (10E,12E,14E)-hexadeca-10,12,14-trienal 1 and the (10E,12E,14Z)-isomer 2, the key pheromone components of the tobacco hornworm moth Manduca sexta. The penultimate (EEZ)-trienol, and aldehyde 1, were freed from isomeric impurities by selective reaction of the impurities with tetracyanoethylene. (EEE)-Aldehyde 2 was prepared by Wittig reaction of (2E,4E)-hexa-2,4-dienyltriphenylphosphonium bromide with 10-acetoxydecanal, deprotection, selective crystallization of the (EEE)-trienol from the resulting mix of isomers, and oxidation. The yield of the (EEE)-trienol was increased further by iodine-catalyzed isomerization of the mix of isomers in the liquor, and further recrystallization.

(10E,12E,14Z)-hexadeca-10,12,14-trienal - (10E,12E,14E)-hexadeca-10,12,14-trienal - tetracyanoethylene - Diels - Alder adduct - pheromone