Russian Chemical Bulletin

, Volume 42, Issue 2, pp 300–306 | Cite as

Terpenes in organic synthesis

14. Synthesis ofS-(+)-hydroprene from (+)-β-citronellene
  • G. D. Gamalevich
  • E. P. Serebryakov
Organic Chemistry


A seven-step synthesis ofS-(+)-hydroprene (S-1) in ∼20 % overall yield starting fromS-(+)-3,7-dimethyl-1,6-octadiene (2) of 55+-10 % optical purity is described. The introduction of an optical enhancement step in the synthetic sequence at the stage ofS-(−)-3,7-dimethyl-1-octanol (9) raises the optical purity ofS-1 from ∼50 % to ∼80 %.

Key words

technical grade β-citronellene S-2,6-dimethyl-7-octen-3-one, Wolff-Kizhner reduction S-3,7-dimethyl-1-octanol, enantiomeric enrichment 


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Copyright information

© Plenum Publishing Corporation 1994

Authors and Affiliations

  • G. D. Gamalevich
    • 1
  • E. P. Serebryakov
    • 1
  1. 1.N. D. Zelinskiy Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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