Journal
ORGANIC LETTERS
Volume 4, Issue 6, Pages 991-994Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol025558l
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[GRAPHICS] Synthesis of N-acyl hemiaminal model systems related to the side chain of the antitumor natural product zampanolide is reported. Key steps involve oxidative decarboxylation of N-acyl-alpha-amino acid intermediates, followed by ytterbium trif late mediated solvolysis. Evidence for stabilization of the N-acyl hemiaminal moiety in model compounds by an intramolecular hydrogen-bonding network is described.
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