TOTAL SYNTHESIS OF THE RACEMIC FORM OF THE SECOND JUVENILE HORMONE (METHYL 12-HOMOJUVENATE) FROM THE CECROPIA SILK MOTH

  1. William S. Johnson,
  2. Simon F. Campbell,
  3. A. Krishnakumaran, and
  4. Andre S. Meyer
  1. DEPARTMENT OF CHEMISTRY, STANFORD UNIVERSITY
  2. DEPARTMENT OF BIOLOGY, CASE WESTERN RESERVE UNIVERSITY

Abstract

Methyl cis-10-epoxy-3,7,11-trimethyl-trans,trans-2,6-tridecadienoate has been stereoselectively synthesized in 12 steps starting from methyl trans-γ-bromo-β,β-dimethylacrylate and 1-acetyl-1-methylcyclopropane. The final product proved to be identical with the second, less abundant juvenile hormone (methyl 12-homojuvenate) isolated from the Cecropia silk moth. The biological activities of the compound were evaluated in various insects.

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  1. PNAS 1969-04 vol. 62 no. 4 1005-1009
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