Transformation of penicillins into 3-substituted Δ3-cephems through addition/cyclization of allenecarboxylates

Bulletin of the Chemical Society of Japan

Volumn 69, Issue 12, 1996, Pages 3651-3658

  Tanaka, Hideo ^a   Sumida, Shin Ichi ^a   Kameyama, Yutaka ^a   Sorajo, Koichi ^a   Wada, Isao ^b   Torii, Sigeru ^a  

^a OKAYAMA UNIVERSITY   (Japan)

^b OTSUKA CHEMICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 CEPHEM 4 CARBOXYLIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030478250     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.69.3651     Document Type: Article

References (35)

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32. 3-cephems 12; see Refs. 9 and 11.
33. 3-cephem 2e was produced more efficiently when the same reaction was carried out in NMP; see Entry 1 in Table 3.
34. The formation of a small amount of monochloro azetidinone 9 can be ascribed to protonation of the intermediate 5f, presumably with a trace amount of water contaminated in the solution. When the reaction was carried out in the presence of N,O-bis(trimethylsilyl)-acetamide for removing the trace amount of water, the side product 9 was not detected. However, the yield of 2f did not significantly change.
35. 3-cephem with the corresponding lithium halides; see Ref. 6b.