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Synthesis of (9R,12S)- and (9S,12S)-Cycloisodityrosine and Their N-Methyl Derivatives
Dale L. Boger1, Jiacheng Zhou, Robert M. Borzilleri
1Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037.
The Journal of Organic Chemistry
|April 4, 1997
Abstract:
Full details of the synthesis of (9R,12S)- and (9S,12S)-cycloisodityrosine and their N-methyl derivatives are detailed based on an intramolecular nucleophilic aromatic substitution reaction for formation of the key biaryl ether with 14-membered ring macrocyclization. Their comparison with prior samples and the documentation of a facile C9 epimerization within the natural 9S series are described.