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An improved preparation of 2-methylene- and 2,3-dimethylenecephalosporins

✍ Scribed by Gunda, Tamas E.

Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
190 KB
Volume
1990
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The one‐step reductive cleavage and reduction of 3‐acetoxymethyl‐2‐methylenecephalosporin sulphoxides provides easy access to 2,3‐dimethylenecephems.

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The title class of 1,l-diactivated ethylenes has been prepared in two steps from aldehydes and t-butyl acrylate by (i) DABCO-catalyzed coupling to give t-butyl 2-(hydroxyalky1)-2-propenoates 11 and (ii) low-temperature Jones oxidation, followed by swift work up at low temperature. The resulting t-bu