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Total Synthesis of Cyclotheonamide C using a Tandem Backbone‐Extension–Coupling Methodology
Author(s) -
Roche Stéphane P.,
Faure Sophie,
Aitken David J.
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200802005
Subject(s) - tandem , chemistry , extension (predicate logic) , combinatorial chemistry , coupling (piping) , stereochemistry , computer science , materials science , programming language , metallurgy , composite material
Mastering unusual amino acids : The first total synthesis of the potent protease inhibitor cyclotheonamide C (see structure representation) has been achieved. The key features of the synthesis are a three‐component tandem procedure to create a masked α‐keto‐β‐arginine within a peptide chain, and the control of the extended conjugation of a vinylogous α,β‐dehydrotyrosine.