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Synthesis 1993; 1993(9): 920-930
DOI: 10.1055/s-1993-25969
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Asymmetric Heck Reaction: Catalytic Asymmetric Syntheses of Bicyclic Enones, Dienones and the Key Intermediate for Vernolepin

Kazuhiro Kondo* , Mikiko Sodeoka, Miwako Mori, Masakatsu Shibasaki
  • *Faculty of Pharmaceutical Sciences, University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113, Japan
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Publication Date:
29 April 2002 (online)

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Bicyclic enone 23a, a functionalized decalin derivative, has been synthesized in up to 86% ee by an asymmetric Heck reaction starting with bisallylic alcohol 24. Enone 23a has been converted to 19, a key intermediate in the synthesis of vernolepin (14). Furthermore, bicyclic dienone 43 has been synthesized in up to 83% ee from the prochiral dienone 39.