Total Synthesis of the Galbulimima Alkaloid (−)-GB17

A tale of two Michaels: The first enantioselective total synthesis of (−)‐GB17 is reported. Construction of this unique naphthoquinolizinone skeleton was achieved by two stereoselective intramolecular Michael additions, one under catalyst control and the other under substrate control.

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2012-03, Vol.51 (10), p.2481-2484
Main Authors: Larson, Reed T., Clift, Michael D., Thomson, Regan J.
Format: Article
Language:English
Subjects:
Alkaloids
Alkaloids - chemical synthesis
Alkaloids - chemistry
Catalysis
Catalysts
Construction
Cyclization
Galbulimima alkaloids
Michael addition
Molecular Structure
Naphthoquinones - chemical synthesis
Naphthoquinones - chemistry
natural product synthesis
organocatalysis
Plant Bark - chemistry
substrate control
Synthesis
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Description
Summary:A tale of two Michaels: The first enantioselective total synthesis of (−)‐GB17 is reported. Construction of this unique naphthoquinolizinone skeleton was achieved by two stereoselective intramolecular Michael additions, one under catalyst control and the other under substrate control.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201108227