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Synthesis 1995; 1995(7): 845-850
DOI: 10.1055/s-1995-4004
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Synthesis of Mono- and Sesquiterpenoids; XXIV: (-)-Homogynolide A, an Insect Antifeedant Isolated from Homogyne alpina

Kenji Mori* , Yoshitaka Matsushima
  • *Department of Agricultural Chemistry, The University of Tokyo, Yayoi 1-1-1, Bunkyo-ku, Tokyo 113, Japan, Fax +81(3)32352214
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Publication Date:
31 December 2000 (online)

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(-)-Homogynolide A (1), an insect antifeedant isolated from Homogyne alpina (Compositae), was synthesized from (1R,4S,6S)-6-hydroxy-1-methylbicyclo[2.2.2]octan-2-one (7), which was readily prepared by the yeast reduction of the corresponding prochiral β-diketone. The key step was the oxy-Cope rearrangement of 6 to give 5.

insect antifeedant - oxy-Cope rearrangement - ring contraction - sesquiterpene - α-spiro-β-methylene-γ-lactone