Studies on Optically Active Amino Acids. IV. A New Synthetic Approach to Chloramphenicol Base from L-Phenylalanine.

Abstract

A new synthetic approach to chloramphenicol base (XVII) was investigated starting with L-phenylalanine (II), making use of the same configuration of the α-carbon in (II) as that of the C-2 in XVII. Preliminary experiments starting with DL-phenylalanine was also described. The synthetic route is shown in Chart 2. threo-XVI and threo-XVII, the final product in this synthetic approach, were isolated from the mixture of threo- and erythro-XV by the application of the stereoselective acyl rearrangement reaction, which is shown in Chart 3.