First chiral synthesis of the N-terminal amino acid congener of nikkomycin Z based on lipase-catalyzed enantioselective acetylation of a primary alcohol possessing two stereogenic centers

Abstract

A stereoselective synthesis of a versatile chiral synthon possessing two stereogenic centers, (2 S,3 S)-3-[2-(5-benzyloxypyridyl)]-2-methyl-1,3-propane diol 12 (>99% ee), was achieved by using a chemo-enzymatic method. The conversion of (2 S,3 S)- 12 to the homochiral intermediate (2 S,3 S,4 S)-2-benzyloxycarbonylamino-4-[2-(5-benzyloxypyridyl)]-4- tert-butyldimethylsilyloxy-3-methylbutanoic acid 2 corresponding to the N-terminal amino acid congener of nikkomycin Z 1 is described.