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Concise and stereoselective synthesis of 2,5- and 2,4-disubstituted thiazole amino acid subunits for synthesizing thiazole-containing peptides

Author:
Magata, Takuji, Hirokawa, Yoshimi, Moriguchi, Yusuke, Yokoi, Ryosuke, Nojiri, Shotaro, Miyazaki, Ryota, Akasako, Sayuri, Takahashi, Rina, Nishida, Munetaka, Hakoda, Junya, Nakayama, Ryota, Tanaka, Aya, Maezaki, Naoyoshi
Source:
Tetrahedron letters 2019 v.60 no.10 pp. 718-720
ISSN:
0040-4039
Subject:
amino acids, catalytic activity, chemical reactions, chemical structure, diastereoselectivity, imines, lithium, palladium, peptides, stereoselective synthesis, thiazoles
Abstract:
A concise, highly stereoselective synthesis of 2,4- and 2,5-disubstituted thiazole amino acids was developed. These are important building blocks for various biologically active thiazole-containing natural peptides and their regioisomeric analogues. The fundamental reactions are diastereoselective addition of (4- or 5-bromothiazol-2-yl)lithium to N-tert-butanesulfinyl imine with subsequent Pd-catalyzed phenoxycarbonylation.
Agid:
6297267