Synthesis of (9R,12S)- and (9S,12S)-Cycloisodityrosine and Their N-Methyl Derivatives

Dale L. Boger; Jiacheng Zhou; Robert M. Borzilleri; Seiji Nukui; Steven L. Castle

doi:10.1021/jo961346o

Synthesis of (9R,12S)- and (9S,12S)-Cycloisodityrosine and Their N-Methyl Derivatives

J Org Chem. 1997 Apr 4;62(7):2054-2069. doi: 10.1021/jo961346o.

Authors

Dale L. Boger¹, Jiacheng Zhou, Robert M. Borzilleri, Seiji Nukui, Steven L. Castle

Affiliation

¹ Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037.

PMID: 11671510
DOI: 10.1021/jo961346o

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.