Cromakalim

It can be used to treat hypertension as it will relax vascular smooth muscle to lower blood pressure.

The course of the reaction can be envisaged by assuming that this then attacks the aromatic ring; the resulting allylic cation can then capture the adjacent phenol oxygen and thus form the observed product (3).

Treatment of that product with aqueous NBS leads to the addition of the elements of hypobromous acid and formation of the bromohydrin (4) as a mixture of the trans enantiomers.

Ring opening of the oxirane with ammonia gives a mixture of the trans amino alcohols (6).

The anion from reaction of the amide with sodium hydride then displaces the chlorine on the end of the chain to form the pyrrolidine ring.

Levcromakalim synthesis: [ 1 ] [ 2 ] racemate: [ 3 ] of isomers: [ 4 ]