Structure and Synthesis of Dopastin, an Inhibitor of Dopamine β-Hydroxylase

Abstract

Dopastin, an inhibitor of dopamine β-hydroxylase of microbial origin, was shown to be N-[2 (S)-nitrosohydroxylamino-3-methylbutyl] crotonamide based on chemical, spectroscopic and synthetic studies. The total synthesis of dopastin was completed in 8 steps starting from L-valinol. N-Nitrosohydroxylamino function was introduced through an oxaziran with retention of the absolute configuration in the final product. Thus, the 2S-configuration of dopastin was proved by the total synthesis. Racemic dopastin was also synthesized from isobutvraldehvde in 7 steps.