DIFFERENT APPROACHES TO THE ASYMMETRIC-SYNTHESIS OF 1,3,6-TRISUBSTITUTED AND 1,2,3,6-TETRASUBSTITUTED CARBAPENEMS(1) FROM D-GLUCOSAMINE

被引：14
|
作者：
ANAYA, J
BARTON, DHR
GERO, SD
GRANDE, M
HERNANDO, JIM
LASO, NM
机构：
[1] TEXAS A&M UNIV,DEPT CHEM,COLLEGE STN,TX 77843
[2] CNRS,INST CHIM SUBST NAT,F-91198 GIF SUR YVETTE,FRANCE
来源：
TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 02期
关键词：
D O I：
10.1016/0957-4166(95)00045-Q
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Different stereocontrolled syntheses of optically active 1,3,6-trisubstituted and 1,2,3,6-tetrasubstituted carbapenems(1) are reported. D-glucosamine, as chiral auxiliary, trans-cinnamaldehyde and methoxyacetyl chloride were used as starting materials in the Staudinger ketene-imine monobactam formation. Radical cyclization and oxidation reactions led to the desired carbapenems.
引用
收藏
页码：609 / 624
页数：16
相关论文
共 50 条
  • [31] Two-step Synthesis of 1, 2, 6-Trisubstituted Benzimidazoles from 3-Fluoro-4-nitrotoluene
    Zhang, Li-Jie
    Li, Chun-Yu
    Jin, Hua-Qiang
    Zhou, Li
    Song, Jia-Liang
    Sun, Ya-Quan
    Jingxi Huagong/Fine Chemicals, 2018, 35 (03): : 443 - 448
  • [32] Recent Developments in the Synthesis of Bioactive 2,4,6-Trisubstituted 1,3,5-Triazines
    Banerjee, Ranjan
    Brown, Douglas R.
    Weerapana, Eranthie
    SYNLETT, 2013, 24 (13) : 1599 - 1605
  • [33] ANTITUMOR ACTIVITY OF SOME NEW 1,3,8-TRISUBSTITUTED PURINE-2,6-DIONES AND 1,3,6-TRISUBSTITUTED THIAZOLO[2,3-f]PURINE-2,4-DIONES
    Hayallah, Alaa M.
    Momekov, Georgi
    Famulok, Michael
    BULLETIN OF PHARMACEUTICAL SCIENCES, 2008, 31 : 391 - 399
  • [34] EFFICIENT SYNTHESIS OF 2',3'-DIDEOXYNUCLEOSIDES AND 2',3'-DIDEOXY C-NUCLEOSIDES FROM D-GLUCOSAMINE
    JUNG, ME
    TRIFUNOVICH, ID
    TETRAHEDRON LETTERS, 1992, 33 (21) : 2921 - 2924
  • [35] Asymmetric synthesis of 1,3,4-trisubstituted pyrrolidines.
    Belyk, K
    Beguin, C
    Palucki, M
    Patel, M
    Dasilva, J
    Askin, D
    Yasuda, N
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 : U32 - U32
  • [36] SYNTHESIS OF 2,3-DISUBSTITUTED AND 2,3,6-TRISUBSTITUTED 1H-INDOL-5-OLS FROM 3-ALKENYLPHENOLS
    SATOMURA, M
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (24): : 6936 - 6938
  • [37] Synthesis of dibenzo[d,g][1,3,6]trithiocins
    Maruta, T
    Sugihara, Y
    Tanaka, S
    Ishii, A
    Nakayama, J
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1998, 71 (05) : 1187 - 1192
  • [38] 1,4-bis(arylsulfonyl)dihydropyridines in synthesis. Enantioselective synthesis of 2,3,6-trisubstituted piperidines
    Carballares, S
    Craig, D
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 624 (1-2) : 380 - 382
  • [39] AN EFFICIENT ASYMMETRIC-SYNTHESIS OF TRISUBSTITUTED CYCLOHEXENONES AND TRISUBSTITUTED CYCLOPENTENONES FROM CHIRAL 2,2-DIALKYL 1,4-DIKETONES AND 1,5-DIKETONES
    MEYERS, AI
    LEFKER, BA
    TETRAHEDRON LETTERS, 1987, 28 (16) : 1745 - 1748
  • [40] Structure-based drug design of 1,3,6-trisubstituted 1,4-diazepan-7-ones as selective human kallikrein 7 inhibitors
    Murafuji, Hidenobu
    Sakai, Hiroki
    Goto, Megumi
    Oyama, Yoshiaki
    Imajo, Seiichi
    Sugawara, Hajime
    Tomoo, Toshiyuki
    Muto, Tsuyoshi
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2018, 28 (08) : 1371 - 1375
12345