137563-63-4Relevant academic research and scientific papers
Application of acyl cyanophosphorane methodology to the synthesis of protease inhibitors: Poststatin, eurystatin, phebestin, probestin and bestatin
Wasserman, Harry H.,Petersen, Anders K.,Xia, Mingde
, p. 6771 - 6784 (2007/10/03)
Full details are given for the syntheses of the protease inhibitors, poststatin and eurystatin by the acyl cyanophosphorane coupling procedure used for the formation of α-keto amides. We have also extended this methodology to the syntheses of the related α-hydroxy amide natural products, phebestin, probestin and bestatin. The key step in the latter synthetic sequences involved diastereomeric selectivity in the reduction of the α-keto precursor to the corresponding α-hydroxy amide by the use of zinc borohydride.
Concise total synthesis of the prolyl endopeptidase inhibitor eurystatin A via a novel Passerini reaction-deprotection-acyl migration strategy
Owens, Timothy D,Araldi, Gian-Luca,Nutt, Ruth F,Semple
, p. 6271 - 6274 (2007/10/03)
The Passerini reaction between suitably protected alaninal, leucine isonitrile, and ornithine components delivered adducts 10a,b in high yield. Orthogonal N-deprotection of 10a led, via a smooth O- to N-acyl migration, to 11, which constitutes the entire skeleton of the eurystatins. Subsequent deprotection, macrocyclization, elaboration, and final oxidation steps efficiently afforded eurystatin A 1a in high overall yield.
The synthesis of eurystatin A1
Schmidt,Weinbrenner
, p. 1003 - 1004 (2007/10/02)
Eurystatin A, a new prolyl endopeptidase inhibitor isolated from Streptomyces eurythermus has now been synthesized.
