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Tetrahedron Letters
Volumn 36, Issue 25, 1995, Pages 4493-4496
Preparation of 3-benzoylpenems and penem amides by wittig methodology
Author keywords

[No Author keywords available]
Indexed keywords

PENEM DERIVATIVE;
EID: 0029032045     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)00767-7     Document Type: Article
Times cited : (7)
References (8)
  • 3
    • 0023664531 scopus 로고
    • A small hydrophobic domain anchors leader peptidase to the cytoplasmic membrane of Escherichia coli.
    • (1987) J Biol Chem , vol.262 , pp. 8806
    • Moore1    Miura2
  • 6
    • 84914005157 scopus 로고    scopus 로고
    • General Procedure. The crude hemi-aminal was treated sequentially with 2,6-lutidine (2 equivalents) and thionyl chloride (2 equivalents) in THF (4ml/mmol of hemi-aminal) at −20°C for 1h. Addition of toluene (12ml/mmol of hemi-aminal), filtration and evaporation of the filtrate to dryness under reduced pressure gave the crude chloro-derivative. Subsequent treatment with triphenylphosphine (4 equivalents) and 2,6-lutidine (2 equivalents) in dioxane (1ml/mmol of hemi-aminal) at RT for 2h gave the required phosphorane.
  • 7
    • 84914005156 scopus 로고    scopus 로고
    • 1-(t-Butyldimethylsilyl)-4-(triphenylmethylthio)azetidin-2-one, prepared by the method of Martel, A. et.al. (Can. J. Chem., 1983, 61, 613), was treated with lithium diisopropylamide at −75°C. After 1h, addition of excess iodoethane and warming to RT over 0.5 h gave the trans-3-ethyl product. Deprotection with potassium fluoride in methanol at 0°C for 2h gave the required trans-3-ethyl-4-(triphenylmethylthio)azetidin-2-one (87%).
  • 8
    • 84914005155 scopus 로고    scopus 로고
    • Addition of fumaryl chloride to pyrrolidine (2.2 equivalents), triethylamine (excess) and catalytic 4-(N,N-dimethylamino)pyridine in dichloromethane at −30°C followed by warming to RT over 4h gave the diamide. Subsequent treatment with ozone at −30°C in dichloromethane for 1h followed by addition of dimethylsulfide (1 equivalent) gave the required 1-(1,2-dioxoethyl)pyrrolidine (40% overall yield).

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.