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A Synthesis‐Driven Structure Revision of Berkelic Acid Methyl Ester
Author(s) -
Buchgraber Philipp,
Snaddon Thomas N.,
Wirtz Conny,
Mynott Richard,
Goddard Richard,
Fürstner Alois
Publication year - 2008
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.200803339
Subject(s) - realization (probability) , chemistry , cascade , stereochemistry , core (optical fiber) , combinatorial chemistry , materials science , mathematics , chromatography , statistics , composite material
A subtle difference : A single step suffices to transform a linear precursor into the chromane spiroketal core of the metalloproteinase‐3 inhibitor berkelic acid by an acid‐catalyzed deprotection/Michael addition/acetalization cascade. This efficient route resulted from the realization that the originally proposed structure is neither thermodynamically nor kinetically favored and has led to revision of the structure (denoted in red).