Synthesis of chiral methyl-branched linear pheromones starting from (+)-aromadendrene. Part 7

Y.M.A.W. Lamers, G. Rusu, J.B.P.A. Wijnberg, Æ. de Groot

Research output: Contribution to journalArticleAcademicpeer-review

19 Citations (Scopus)

Abstract

Ethyl (7S)-10-hydroxy-7-methyldecanoate (4), a linear methyl-branched intermediate with its chiral center at C7, and with two different functional groups at the ends of the chain, has been synthesized from (+)-aromadendrene in nine steps. A Baeyer-Villiger oxidation and a Grob fragmentation are the key reactions in this transformation. Intermediate 4 has been applied in the synthesis of three linear methyl-branched pheromones, (i) (R)-10-methyl-2-tridecanone, the active pheromone of the southern corn rootworm Diabrotica undecimpunctata howardi Barber, (ii) (S)-9-methylnonadecane, one of the sex pheromones of the cotton leafworm Alabama argillacea, and (iii) (meso)-13,23-dimethylpentatriacontane, the sex pheromone of the tse tse fly Glossina pallidipes. (C) 2003 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)9361-9369
Number of pages8
JournalTetrahedron
Volume59
DOIs
Publication statusPublished - 2003

Keywords

  • southern corn-rootworm
  • diabrotica-undecimpunctata-howardi
  • sex-pheromone
  • natural (+)-aromadendrene
  • rearrangement reactions
  • stereoisomers
  • conversion
  • chemistry
  • synthons

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