Russian Chemical Bulletin

, Volume 49, Issue 4, pp 717–721 | Cite as

Synthesis of (S)-6-methylhept-5-en-2-ol, the aggregation pheromone ofGnathotrichus sulcatus

  • G. Yu. Ishmuratov
  • R. Ya. Kharisov
  • M. P. Yakovleva
  • R. R. Muslukhov
  • E. G. Galkin
  • V. S. Shmakov
  • T. V. Khakimova
  • G. A. Tolstikov
Organic Chemistry

Abstract

An enantioselective (ee−50%) four-step synthesis of (S)-6-methylhept-5-en-2-ol (“sulcatol”), which is the aggregation pheromone ofGnathotrichus sulcatus, from 3S,7-dimethylocta-1,6-diene was developed.

Key words

linear isoprenoids (S)-6-methylhept-5-en-2-ol aggregation pheromone ambrosia beetle 3S,7-dimethyloct-6-en-2-one Baeyer—Villiger reaction peroxy acid epoxidation (2S,5R/S)-2-acetoxy-5,6-dibromo-6-methylheptane 4S,5,7,7-tetramethyl-6,8-dioxabicyclo[3.2.1]octane 

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Copyright information

© Kluwer Academic/Plenum Publishers 2000

Authors and Affiliations

  • G. Yu. Ishmuratov
    • 1
  • R. Ya. Kharisov
    • 1
  • M. P. Yakovleva
    • 1
  • R. R. Muslukhov
    • 1
  • E. G. Galkin
    • 1
  • V. S. Shmakov
    • 1
  • T. V. Khakimova
    • 1
  • G. A. Tolstikov
    • 1
  1. 1.Institute of Organic ChemistryUfa Research Center of the Russian Academy of SciencesUfaRussian Federation

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