A Non Ozone Approach to Enol Azetidinones: Synthetic Precursors to β-Lactam Antibiotics

Jeanine Thomas; Joydeep Kant

doi:10.1055/s-1993-25850

Synthesis 1993; 1993(3): 293-295
DOI: 10.1055/s-1993-25850

short paper

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A Non Ozone Approach to Enol Azetidinones: Synthetic Precursors to ß-Lactam Antibiotics

Jeanine Thomas^* , Joydeep Kant

^*Bristol-Myers Squibb Pharmaceutical Research Institute, 5 Research Parkway, P.O. Box 5100, Wallingford, Connecticut 06492-7660, USA

Abstract

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The enol-substituted azetidininones (diphenylmethyl 2-[(3R, 4R)- 4-(2-benzothiazolyldithio)-2-oxo-3-(phenoxyacetylamino)-1-azetidinyl]-3-hydroxy-2-butenoate and derivatives) are valuable intermediates in the synthesis of a variety of cephalosporins. A combination of osmium tetroxide/sodium periodate oxidative system has been developed to prepare these intermediates in high yields. The methodology represents an alternative to ozonolysis.

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