Total Synthesis of (+)-Apiosporamide: Assignment of Relative and Absolute Configuration

Antipodal relationship: A convergent synthetic pathway leading to 4‐hydroxy‐2‐pyridinones was involved in the synthesis of apiosporamide (1) and YM‐215343 (2). Both have an antipodal relationship to the natural metabolites, whose relative and absolute configurations have been established. Activated...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2005-10, Vol.44 (41), p.6715-6718
Main Authors: Williams, David R., Kammler, David C., Donnell, Andrew F., Goundry, William R. F.
Format: Article
Language:English
Subjects:
antifungal agents
antitumor agents
Cyclohexanols - chemical synthesis
Cyclohexanols - chemistry
heterocycles
lactams
Molecular Conformation
Naphthalenes - chemical synthesis
Naphthalenes - chemistry
Optical Rotation
Pyridones - chemical synthesis
Pyridones - chemistry
Stereoisomerism
total synthesis
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Summary:Antipodal relationship: A convergent synthetic pathway leading to 4‐hydroxy‐2‐pyridinones was involved in the synthesis of apiosporamide (1) and YM‐215343 (2). Both have an antipodal relationship to the natural metabolites, whose relative and absolute configurations have been established. Activated β‐alanine enolate equivalents derived from β‐lactams were the key to the synthesis.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200502015