Enantiocontrolled Synthesis and Absolute Configuration of (+)-Crooksidine, An Indole Alkaloid from Haplophyton Crooksii Using Chiral Piperideinol Block

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Abstract
(+)-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.

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