Synthesis-Driven Structure Revision of Berkelic Acid Methyl Ester

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 origi...

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Veröffentlicht in:	Angewandte Chemie (International ed.) 2008-10, Vol.47 (44), p.8450-8454
Hauptverfasser:	Buchgraber, Philipp, Snaddon, Thomas N, Wirtz, Conny, Mynott, Richard, Goddard, Richard, Fürstner, Alois
Format:	Artikel
Sprache:	eng
Schlagworte:	anticancer agents enzyme inhibitors Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacology Esters - chemical synthesis Esters - chemistry Esters - pharmacology Magnetic Resonance Spectroscopy Matrix Metalloproteinase Inhibitors natural products Spiro Compounds - chemical synthesis Spiro Compounds - chemistry Spiro Compounds - pharmacology spiroacetals Stereoisomerism structure elucidation Structure-Activity Relationship
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Beschreibung
Zusammenfassung:	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).
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.200803339