Synthesis of N-Substituted phosphoramidic acid esters as 'reverse' fosmidomycin analogues

摘要

An efficient synthetic pathway to a series of novel "reverse" fosmidomycin analogues has been developed, commencing from substituted benzylamines. In these analogues, the fosmidomycin hydroxamate moiety is reversed and the tetrahedral methylene carbon adjacent to the phosphonate moiety is replaced by a nitrogen atom bearing different benzyl groups. The resulting phosphonate esters were designed as potential antimalarial "pro-drugs". (C) 2019 Elsevier Ltd. All rights reserved.