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Total Synthesis and Stereochemical Reassignment of (±)‐Indoxamycin B
Author(s) -
Jeker Oliver F.,
Carreira Erick M.
Publication year - 2012
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.201109175
Subject(s) - sequence (biology) , core (optical fiber) , computer science , steric effects , total synthesis , information retrieval , product (mathematics) , natural (archaeology) , stereochemistry , chemistry , world wide web , combinatorial chemistry , mathematics , history , telecommunications , biochemistry , geometry , archaeology
Revised version : The first total synthesis of indoxamycin B leads to a stereochemical reassignment of the natural product (see picture). The synthetic route features an efficient carboannulation sequence to rapidly access the dihydroindenone system. Moreover, a series of Au I ‐catalyzed transformations served in the construction of the sterically congested core framework.