Synthesis of biologically interested anhydropenicillin derivatives

MALIANDI, CARLA; MASCARETTI, ORESTE A; MATA, ERNESTO G.

Journal of Undergraduate Chemistry Research

Chemistry Dep., Virginia Military Inst.

Lugar: Lexington; Año: 2002 vol. 1 p. 127 - 130

1541-6003

The preparation of 3?Z-substituted anhydropenicillins in three steps from the versatile unsymmetrical disulfides 1a,b is described. Key step is the conversion of 2-methyl substituted penicillanic acids into anhydropenicillins by the Wolfe rearrangement. 3?Z-substituted anhydropenicillins are interesting in the area of prodrugs for potential interaction with monoclonal antibody--lactamase tumor targeting systems