135219-43-1Relevant articles and documents
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.
A convergent synthesis of poststatin: Application of the acyl cyanophosphorane coupling procedure in the formation of a peptidic α-keto amide
Wasserman, Harry H.,Petersen, Anders K.
, p. 953 - 956 (2007/10/03)
A convergent synthesis of the pentapeptide poststatin has been developed. The key step involves oxidative cleavage of an acyl cyanophosphorane. The resulting α,β-diketo nitrile is then coupled to the free amine of a C-terminal-dipeptidyl component to generate the protected natural product. Deprotection by hydrogenolysis furnishes poststatin.
