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Total Synthesis of (+)‐Apiosporamide: Assignment of Relative and Absolute Configuration
Author(s) -
Williams David R.,
Kammler David C.,
Donnell Andrew F.,
Goundry William R. F.
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200502015
Subject(s) - antipodal point , content (measure theory) , key (lock) , stereochemistry , total synthesis , computer science , absolute (philosophy) , chemistry , combinatorics , mathematics , philosophy , epistemology , mathematical analysis , geometry , computer security
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.