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Russian Chemical Bulletin

, Volume 42, Issue 1, pp 100–101 | Cite as

Synthesis ofS-(+)-hydroprene

  • V. N. Odinokov
  • G. Yu. Ishmuratov
  • R. Ya. Kharisov
  • E. P. Serebryakov
  • G. A. Tolstikov
Organic Chemistry

Abstract

A novel path toS-(+)-hydroprene (1) starting from the technical gradeS-(+)-dihydromyrcene (2, e.e. ⩾50%) is proposed. The latter was selectively transformed intoS-3,7-dimethyloctanal (5) in three steps including hydroalumination. The reactions of5 with allyl- or methallylmagnesium chloride followed, respectively, either by oxygenation in the presence of PdCl2/CuCl or by ozonolysis, affordS,E-6,10-dimethyl-3-undecen-2-one (7) which was treated with ethoxyethynylmagnesium bromide to give the title juvenile hormone analogue in ∼23% overall yield.

Key words

ethylS-3,7,11-trimethyl-2E,4E-dodecadienoate, synthesis S-3,7-dimethyl-1,6-octadiene, hydroalumination S-3,7-dimethyloctanal 6S, 10-dimethyl-1-undecen-4R/S-ol 2,6S,10-trimethyl-1-undecen-4R/S-ol, ozonolysis S,E-6,10-dimethyl-3-undecen-2-one 

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Copyright information

© Plenum Publishing Corporation 1993

Authors and Affiliations

  • V. N. Odinokov
    • 1
  • G. Yu. Ishmuratov
    • 1
  • R. Ya. Kharisov
    • 1
  • E. P. Serebryakov
    • 2
  • G. A. Tolstikov
    • 1
  1. 1.Institute of Organic Chemistry, the Ural BranchRussian Academy of SciencesUfaRussian Federation
  2. 2.N.D.Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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