SYNTHESIS OF (9R,12S)-CYCLOISODITYROSINE AND (9S,12S)-CYCLOISODITYROSINE AND THEIR N-METHYL DERIVATIVES

Authors
BOGER DL ZHOU JC BORZILLERI RM NUKUI S CASTLE SL
Citation
Dl. Boger et al., SYNTHESIS OF (9R,12S)-CYCLOISODITYROSINE AND (9S,12S)-CYCLOISODITYROSINE AND THEIR N-METHYL DERIVATIVES, Journal of organic chemistry, 62(7), 1997, pp. 2054-2069
Citations number
43
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
62
Issue
7
Year of publication
1997
Pages
2054 - 2069
Database
ISI
SICI code
0022-3263(1997)62:7<2054:SO(A(>2.0.ZU;2-T
Abstract
Full details of the synthesis of (9R,12S)- and (9S,12S)-cycloisodityro sine and their N-methyl derivatives are detailed based on an intramole cular nucleophilic aromatic substitution reaction for formation of the key biaryl ether with 14-membered ring macrocyclization. Their compar ison with prior samples and the documentation of a facile C9 epimeriza tion within the natural 9S series are described.