Formal synthesis of (-)-codeine by application of temporary thio derivatization.

Rautschek J, Jäger A, Metz P (2018) Formal synthesis of (-)-codeine by application of temporary thio derivatization. Org Lett 20(3), 832-835.

Abstract

Desymmetrization of a p-quinone monoacetal by organocatalytic sulfa-Michael addition provided rapid access to a C-ring building block for a formal synthesis of (-)-codeine. By means of a diastereoselective 1,2-addition for A/C-ring union, an intramolecular nitrone cycloaddition for construction of the phenanthrene core, and a sulfoxide elimination, an enantiopure key intermediate of the authors' previous synthesis of racemic codeine was available in 12 steps from isovanillin.

Leibniz-HKI-Authors

Julia Rautschek

Identifier

doi: 10.1021/acs.orglett.7b03972

PMID: 29356553