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Iterative Oxazole Assembly via α‐Chloroglycinates: Total Synthesis of (−)‐Muscoride A
Author(s) -
Coqueron PierreYves,
Didier Charles,
Ciufolini Marco A.
Publication year - 2003
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.200390363
Subject(s) - oxazole , total synthesis , natural product , reagent , scheme (mathematics) , combinatorial chemistry , computer science , chemistry , mathematics , stereochemistry , organic chemistry , mathematical analysis
An efficient iterative synthesis of oxazoles involves the cyclization of 2‐alkynyl glycinates (see scheme) formed from the reaction of 1‐alkynyl aluminum reagents with α‐chloroglycinates. This approach was used in the total synthesis of the bisoxazole natural product, (−)‐muscoride A.