Organolithium-mediated diversification of peptide thiazoles.
[Reaction: see text] We report a one-step, racemization-free method for the diversification of peptide thiazoles via direct lithiation of the thiazole ring. The method is compatible with N-Boc, N-trityl, carboxylic ester, and carboxamide protecting groups and has been used to directly functionalize the thiazole ring of cyclopeptide natural products.
Deng
Shaojiang
S
Department of Cellular and Molecular Pharmacology, University of California, San Francisco, 600 16th Street, San Francisco, California 94143, USA.
Taunton
Jack
J
D008094:Lithium / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry* / Q000378:metabolism; D013844:Thiazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism
D009942:Organometallic Compounds; D010455:Peptides; D013844:Thiazoles; D008094:Lithium