A versatile, enantioselective, stereocontrolled synthesis of (1S,2R)-imidazoleglycerol
An efficient (21% overall yield), enantio- and diastereoselective, 11-step synthesis of (1S,2R)-imidazoleglycerol has been developed. The key steps are the stereoselective hydroxylation of an acyloxazolidinone enolate, the alkylation of a thioester with (MOMOCH2)2CuLi and the stereodivergent reduction of the resulting ketone. The scope of the reaction of the enolate derived from 10 with heteroatom electrophiles has been studied.
Paz, Manuel M.,Correa, Juan F.,Cabeza, M. Isabel,Sardina, F. Javier