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Synlett 1999; 1999(6): 774-776
DOI: 10.1055/s-1999-2735
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Synthesis of 3-Alkenyl-Δ3-cephems via Sequential Reductive 1,2-Elimination/Addition/Cyclization in an Alkenyltin/Copper(I) Chloride/bpy System

Hideo Tanaka* , Yoshihisa Tokumaru, Sigeru Torii
  • *Department of Applied Chemistry, Faculty of Engineering, Okayama University, Tsushima-naka 3-1-1, Okayama, Okayama 700-8530, Japan; E-mail: tanaka95@cc.okayama-u.ac.jp
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Publication Date:
31 December 1999 (online)

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A sequential reductive 1,2-elimination-addition-cyclization of 3,4-disubstituted butenoates derived from penicillin is performed successfully by treatment with alkenyltin, copper(I) chloride and 2,2′-bipyridine (bpy) in N-methyl-2-pyrrolidinone (NMP) to afford 3-alkenyl-Δ3-cephems.

3-alkenyl-Δ3-cephems - 3,4-disubstituted butenoate - reductive 1,2-elimination - addition/cyclization - alkenyltin/CuCl system