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Synlett 1996; 1996(2): 163-164
DOI: 10.1055/s-1996-5365
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Enantiocontrolled Synthesis and Absolute Configuration of (+)-Crooksidine, An Indole Alkaloid from Haplophyton Crooksii Using Chiral Piperideinol Block

Hideki Sakagami, Kiyohiro Samizu, Takashi Kamikubo, Kunio Ogasawara*
  • *Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-77, Japan, Fax +81-22-217-6846; E-mail c21799@cctu.cc.tohoku.ac.jp
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Publication History

Publication Date:
31 December 2000 (online)

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(+)-Crooksidine has been synthesized first time starting from the optically pure (S)-3-piperidein-5-ol resolved by lipase-mediated kinetic transesterification. The key synthetic intermediate has also furnished another indole alkaloid (+)-(R)-decarbomethoxy-15,20:16,17-tetrahydrosecodine, occurred in the same plant, which has concluded the absolute configuration of (+)-crooksidine as R as well as that of the starting piperideinol as S.

lipase-mediated resolution - chiral piperideinol block - absolute configuration of crooksidine - indole alkaloid