2003Angewandte Chemie International EditionRequires access

Enantioselective Total Syntheses of the Cyclotryptamine Alkaloids Hodgkinsine and Hodgkinsine B

Jeremy J. Kodanko, Larry E. Overman

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Abstract

A late-stage resolution of the meso-3a,3a′-bispyrrolidinoindoline unit of rac-7 in a catalytic asymmetric transformation earmarks the remarkably short, ten-step, total syntheses of hodgkinsine and hodgkinsine B. The enantioselective total synthesis of hodgkinsine B establishes the relative and absolute configuration of this trispyrrolidinoindoline alkaloid.

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A late-stage resolution of the meso-3a,3a′-bispyrrolidinoindoline unit of rac-7 in a catalytic asymmetric transformation earmarks the remarkably short, ten-step, total syntheses of hodgkinsine and hodgkinsine B. The enantioselective total synthesis of hodgkinsine B establishes the relative and absolute configuration of this trispyrrolidinoindoline alkaloid.

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Available abstract

A late-stage resolution of the meso-3a,3a′-bispyrrolidinoindoline unit of rac-7 in a catalytic asymmetric transformation earmarks the remarkably short, ten-step, total syntheses of hodgkinsine and hodgkinsine B. The enantioselective total synthesis of hodgkinsine B establishes the relative and absolute configuration of this trispyrrolidinoindoline alkaloid.

Key concepts: Enantioselective synthesis, Total synthesis, Chemistry, Stereochemistry, Absolute configuration, Alkaloid, Catalysis, Organic chemistry

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Enantioselective Total Syntheses of the Cyclotryptamine Alkaloids Hodgkinsine and Hodgkinsine B — Research Paper | ScholarLens