1033722-47-2Relevant academic research and scientific papers
Total syntheses of bistratamides J, E, and H from two types of δala-containing oligopeptides
Suzuki, Hiroyuki,Andoh, Masanori,Yonezawa, Yasuchika,Akai, Shoji,Shin, Chung-Gi,Sato, Ken-Ichi
experimental part, p. 495 - 501 (2009/04/10)
The total syntheses of naturally occurring bis- and tris(heterocyclic) cyclopeptide bistratamides J (1), H (2), and E (3) from two types of dehydropeptides are described. The strategy involves the preparation of the promising building blocks: N-{2-[(S)-l-(N-benzyloxycarbonyl)amino-2- methylpropyl]thiazol-4-ylcarbonyl}-L-Val-(5)NH2 (4) as the left-half component, and methyl N-(3-bromo-2-oxopropanoyl)-L-Val-O-(tert- butyldiphenylsilyl)-L-threonate (5) as the right- half. The subsequent Hantzsch thiazole synthesis between 4 and 5 afforded a linear N,O-protected bis(heteroeyclic)pep-tide as the precursor of 1. Upon deprotection, the precursor was converted to 1 via macrocyclization under high-dilution condition, using BOP [benzotriazol-l-yloxytris(dimethylamino)phosphonium hexafiuorophosphate] as the condensing agent. Furthermore, 1 was converted to 2, which was transformed into 3 via ring-opening and re-oxazolination.
