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Communication | Special issue | Vol 15, No. 2, 1981, pp.785-789
Published online, 1st January, 1970
DOI: 10.3987/S-1981-02-0785
Synthesis of Optically Active(5R,3S)-1-Deoxa-1-thia Analogues of Clavulanic Acid from Penicillanic Acid Derivatives

Maurizio Foglio, Giovanni Franceschi,* Guido Serra-Errante, Marzia Ballabio, and Federi-co Arcamone

*Farmitalia Carlo Erba S.p.A, Ricerca & Sviluppo Chimico, Via dei Gracchi,35 20146 Milan, Italy

Abstract

A novel synthesis of the chiral 1-thiaclavulanic skeleton consisting in the trapping reaction of penicillinate-S-oxide and glutinic acid dimethylester followed by demolition of the N-appendage and rebuilding of the thiazolidine ring is reported. Stereochemical assignements of the products are also discussed.