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Synlett 1991; 1991(12): 888-890
DOI: 10.1055/s-1991-20912
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A New Short Cut Route to 3-Norcephalosporins1

Hideo Tanaka* , Yutaka Kameyama, Shin-ichi Sumida, Takae Yamada, Yoshihisa Tokumaru, Takashi Shiroi, Michio Sasaoka, Masatoshi Taniguchi, Sigeru Torii
  • *Department of Applied Chemistry, Faculty of Engineering, Okayama University, Okayama 700, Japan
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Publication Date:
07 March 2002 (online)

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3-Norcephems 1 bearing heteroatom substituents directly attached to C(3)-position were prepared starting from penicillin G through a new short cut route involving Michael addition of amines, azide or thiols to allenic esters 6, 2-[2-oxo-3-phenylacetylamino-4-(phenylsulfonylthio)azetidin-1-yl]-2,3-butadienoic acid esters, and sequential ring closure to the six-membered ring.