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Terpenes in organic synthesis 13. Synthesis of s-(+)-methoprene from (+)-β-citronellene

  • É. P. Serebryakov
  • G. M. Zhdankina
  • G. V. Kryshtal'
  • M. V. Mavrov
  • Nguen Kong Khao
Organic Chemistry
  • 101 Downloads

Abstract

S-(+)-Methoprene (I) was synthesized from (+)-β-citronellene (III) with an optical purity of about 50%. The optical purity of the key intermediate, S-(−)-7-methoxy-3,7-dimethyl-1-octanol (IV), can be increased by fractional crystallization of the optically active acid phthalate salt (VI) followed by hydrolytic regeneration of alcohol (IV). The yield of (I) at the final synthetic stage can be increased by use of interphase catalysis. S-(+)-Methoprene has a higher morphogenetic activity than the racemic form.

Keywords

Alcohol Crystallization Catalysis Phthalate Terpene 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1991

Authors and Affiliations

  • É. P. Serebryakov
    • 1
  • G. M. Zhdankina
    • 1
  • G. V. Kryshtal'
    • 1
  • M. V. Mavrov
    • 1
  • Nguen Kong Khao
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

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