Studies Toward the Synthesis of (−)-Zampanolide: Preparation of N-Acyl Hemiaminal Model Systems
- 1 March 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 4 (6) , 991-994
- https://doi.org/10.1021/ol025558l
Abstract
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-α-amino acid intermediates, followed by ytterbium triflate mediated solvolysis. Evidence for stabilization of the N-acyl hemiaminal moiety in model compounds by an intramolecular hydrogen-bonding network is described.Keywords
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