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Volumn 45, Issue 6, 1980, Pages 1130-1135

Thienamycin Total Synthesis. 1. Synthesis of Azetidinone Precursors of (±)-Thienamycin and Its Stereoisomers

Author keywords

[No Author keywords available]

Indexed keywords

AZETIDINONE DERIVATIVE; THIENAMYCIN;

EID: 0018870715     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo01294a042     Document Type: Article
Times cited : (78)

References (30)
  • 8
    • 37049092557 scopus 로고
    • For recent reviews see: (a)
    • For recent reviews see: (a) N. S. Isaacs, Chem. Soc. Rev., 5, 181 (1976)
    • (1976) Chem. Soc. Rev. , vol.5 , pp. 181
    • Isaacs, N.S.1
  • 11
    • 0000726270 scopus 로고
    • This diene is a mixture of E/Z isomers; however, this fact is of no consequence as the double bond is subsequently reduced.
    • H. C. Hagemeyer and D. C. Hull, Ind. Eng. Chem., 41, 2920 (1949). This diene is a mixture of E/Z isomers; however, this fact is of no consequence as the double bond is subsequently reduced.
    • (1949) Ind. Eng. Chem. , vol.41 , pp. 2920
    • Hagemeyer, H.C.1    Hull, D.C.2
  • 23
    • 85021541164 scopus 로고    scopus 로고
    • Since steric crowding on the endo face of the cis mesylate prevents the mesyloxy group and H(6) from readily achieving the anti relationship necessary for facile E2 elimination, it is not surprising that, in this case, other pathways are found, and a mixture of ene lactams results.
    • A similar mesylation-elimination sequence performed on cis carbinol lib gave ene lactams 13 and 14 in a ratio of 2:1, respectively. Since steric crowding on the endo face of the cis mesylate prevents the mesyloxy group and H(6) from readily achieving the anti relationship necessary for facile E2 elimination, it is not surprising that, in this case, other pathways are found, and a mixture of ene lactams results.
    • A similar mesylation-elimination sequence performed on cis carbinol lib gave ene lactams 13 and 14 in a ratio of 2:1, respectively.
  • 25
    • 85007833697 scopus 로고
    • Report ORNL-3794 (2nd revision, with supplemental instructions), U.S. Atomic Energy Commission, Oak Ridge National Laboratory, Oak Ridge, TN
    • C. A. Johnson, “ORTEP-II: A Fortran Thermal-Ellipsoid Plot Program for Crystal Structure Illustrations”, Report ORNL-3794 (2nd revision, with supplemental instructions), U.S. Atomic Energy Commission, Oak Ridge National Laboratory, Oak Ridge, TN, 1970.
    • (1970) ORTEP-II: A Fortran Thermal-Ellipsoid Plot Program for Crystal Structure Illustrations
    • Johnson, C.A.1
  • 29
    • 0003987705 scopus 로고
    • Version of June 1972: TR-192”, Computer Science Center, University of Maryland, College Park, MD
    • J. M. Stewart, G. J. Kruger, H. L. Ammon, C. Dickinson, and S. R. Hall, “The X-ray System, Version of June 1972: TR-192”, Computer Science Center, University of Maryland, College Park, MD, 1972.
    • (1972) The X-ray System
    • Stewart, J.M.1    Kruger, G.J.2    Ammon, H.L.3    Dickinson, C.4    Hall, S.R.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.