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Total Synthesis of Thiostrepton, Part 2: Construction of the Quinaldic Acid Macrocycle and Final Stages of the Synthesis
Author(s) -
Nicolaou K. C.,
Zak Mark,
Safina Brian S.,
Lee Sang Hyup,
Estrada Anthony A.
Publication year - 2004
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.200461341
Subject(s) - moiety , chemistry , thiostrepton , dipeptide , thiazoline , total synthesis , stereochemistry , amine gas treating , enantiopure drug , medicinal chemistry , enantioselective synthesis , amino acid , organic chemistry , catalysis , gene , ribosome , rna , biochemistry
The flagship of the thiopeptide class of antibiotics, thiostrepton (see formula), was synthesized by fusion of the quinaldic acid moiety onto the dehydropiperidine–thiazoline macrocycle (see above) followed by demasking of its sensitive functionalities.