Structure and synthesis of dopastin, an inhibitor of dopamine .BETA.-hydroxylase.
Open Access
- 1 January 1974
- journal article
- Published by Oxford University Press (OUP) in Agricultural and Biological Chemistry
- Vol. 38 (11) , 2099-2105
- https://doi.org/10.1271/bbb1961.38.2099
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.Keywords
This publication has 0 references indexed in Scilit: