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Synthesis 2000; 2000(13): 1825-1834
DOI: 10.1055/s-2000-8235
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Diastereodivergent Synthesis of the C9-Cyclopentanone Chiral Building Blocks

Hiroshi Nagata* , Mitsuhiro Kawamura, Kunio Ogasawara
  • *Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan; Fax +81(22)217-6845; E-mail: konol@mail.cc.tohoku.ac.jp
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Publication Date:
31 December 2000 (online)

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Diastereodivergent synthesis the C9-cyclopentanone chiral building block, serving as the non-tryptamine moiety of the Corynanthe type indole alkaloids and the related natural products, and its diastereomer has been developed from racemic norcamphor by employing lipase-mediated resolution via an allylic acetate intermediate having a bicyclo[3.2.1]octane framework. A potential of the latter diastereomer has been demonstrated by its conversion into (-)-semburin, a monoterpene isolated from Swertia japonica previously and obtained from the C9-block.

lipase-mediated kinetic resolution - enantioconvergent synthesis - diastereoconvergent synthesis - enantiodivergent synthesis - diastereodivergent synthesis - chiral building block - ring expansion