Synthesis of 2-exo-Methylenepenam and 3-Chloro-Δ3-cephem through a Sequential Reductive 1,2-Elimination/S-S Bond Fission or Chloride Ion-Addition/Cyclization of 3,4-Disuhstituted 2-Butenoates in Metal Salt/Metal Combinations

Journal of Organic Chemistry

Volumn 62, Issue 11, 1997, Pages 3610-3617

  Tanaka, Hideo ^a   Sumida, Shin Ichi ^a   Nishioka, Yoichi ^a   Kobayashi, Noriko ^a   Tokumaru, Yoshihisa ^a   Kameyama, Yutaka ^a   Torii, Sigeru ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 AZETIDINONE DERIVATIVE; 2 METHYLENEPENAM; 3 CHLOROCEPHEM; CEPHEM DERIVATIVE; PENAM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIC POTENTIOMETRY; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030977334     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970051n     Document Type: Article

References (29)

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29. The formation of 10 can be rationalized by a sequential reaction involving a two-electron reduction of the chlorine atom of 6 leading to the corresponding anion and the nucleophilic attack of the terminal carbanion to the (phenylsulfonyl)thio group. The further reduction of C(3)-substituent (Z = OTs) of the cephem 10c with the metal/metal salt combination would give the 3-norcephem 11.