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1. A versatile, enantioselective, stereocontrolled synthesis of (1S,2R)-imidazoleglycerol

Author

Juan F. Cornea, Manuel M. Paz, F. Javier Sardina, and M. Isabel Cabeza

Subjects
chemistry.chemical_classification, Ketone, Chemistry, Stereochemistry, Organic Chemistry, Heteroatom, Enantioselective synthesis, Alkylation, Thioester, Biochemistry, Hydroxylation, chemistry.chemical_compound, Drug Discovery, Electrophile, Stereoselectivity
Abstract

An efficient (21% overall yield), enantio- and diastereoseleclive, 11-step synthesis of (1 S ,2 R )-imidazoleglycerol has been developed. The key steps are the stereoselective hydroxylation of an acyloxazolidinone enolate, the alkylation of a thioester with (MOMOCH 2 ) 2 CuLi 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.

Published
1996
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