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Stereocontrolled Synthesis of the Quinaldic Acid Macrocyclic System of Thiostrepton
Author(s) -
Nicolaou K. C.,
Safina Brian S.,
Funke Christian,
Zak Mark,
Zécri Frédéric J.
Publication year - 2002
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 - 10.1002/1521-3773(20020603)41:11<1937::aid-anie1937>3.0.co;2-y
Subject(s) - thiostrepton , moiety , chemistry , ring (chemistry) , stereochemistry , thiazole , amide , combinatorial chemistry , organic chemistry , ribosome , rna , biochemistry , gene
An efficient construction of the quinaldic acid macrocycle (see picture) of the antibiotic thiostrepton is based on state‐of‐the‐art asymmetric synthesis. The 27‐membered macrocycle includes a quinaldic acid moiety, a thiazole ring, and a dehydroalanine unit. The key steps in the convergent assembly included: a) amide bond formation, b) esterification, and c) macrolactamization.