Versatile strategy for the solid phase synthesis of penicillin derivatives: efficient preparation of 2b-methyl substituted penams as b-lactamase inhibitor analogues

ERNESTO G. MATA; BOGGIAN, DORA

SYNTHESIS

Thieme

Lugar: Stuttgart; Año: 2006 vol. 2006 p. 3397 - 3404

1414-915X

We describe the development of a convenient method for the synthesis of 2b-methyl substituted penicillins using the commercially available resins. Functionalization of Merrifield and Wang resin bound-penam derivatives was performed by penicillin sulfoxide rearrangement and releasing from the supports were carried out under mild conditions. The utility of this methodology have been demonstrated by synthesizing a small library of penicillin derivatives in moderate to very good overall isolated yields for the multistep synthetic sequence.