Preparation of aminated taxol side chain precursors. A simple approach to 2,3-diamino acids using the beta-lactam synthon method.

被引:23
作者
Moyna, G [1 ]
Williams, HJ [1 ]
Scott, AI [1 ]
机构
[1] TEXAS A&M UNIV,DEPT CHEM,CTR BIOL NMR,COLLEGE STN,TX 77843
关键词
D O I
10.1080/00397919708006094
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Coupling-ready aminated side chain analog precursors of the anticancer drug taxol were prepared through the beta-lactam synthon method. The procedure described represents an easy connection between beta-lactams and 2,3-diamino acids, is highly stereospecific, and causes no racemization due to vicinal group participation.
引用
收藏
页码:1561 / 1567
页数:7
相关论文
共 19 条
  • [1] ARBUCK SG, 1995, TAXOL SCI APPL, pCH14
  • [2] CHEMOENZYMATIC SYNTHESIS OF THE C-13 SIDE-CHAIN OF TAXOL - OPTICALLY-ACTIVE 3-HYDROXY-4-PHENYL BETA-LACTAM DERIVATIVES
    BRIEVA, R
    CRICH, JZ
    SIH, CJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05) : 1068 - 1075
  • [3] A HIGHLY EFFICIENT, PRACTICAL APPROACH TO NATURAL TAXOL
    DENIS, JN
    GREENE, AE
    GUENARD, D
    GUERITTEVOEGELEIN, F
    MANGATAL, L
    POTIER, P
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (17) : 5917 - 5919
  • [4] SYNTHESIS OF TRANS-1-P-METHOXYPHENYL-3-ACETOXY-4-PHENYLAZETIDIN-2-ONE - A KEY STARTING BETA-LACTAM FOR 2'-EPI-TAXOL
    ENDO, M
    DROGHINI, R
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (11) : 2483 - 2486
  • [5] SYNTHESIS OF BIOLOGICALLY-ACTIVE TAXOL ANALOGS WITH MODIFIED PHENYLISOSERINE SIDE-CHAINS
    GEORG, GI
    CHERUVALLATH, ZS
    HIMES, RH
    MEJILLANO, MR
    BURKE, CT
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (22) : 4230 - 4237
  • [6] GEORG GI, 1993, ORGANIC CHEM BETA LA
  • [7] GEORG GI, 1995, TAXOL SCI APPL, pCH13
  • [8] GEORG GI, 1994, ACS S SERIES, V583, pCH16
  • [9] STUDIES TOWARD STRUCTURE-ACTIVITY-RELATIONSHIPS OF TAXOL(R) - SYNTHESIS AND CYTOTOXICITY OF TAXOL(R) ANALOGS WITH C-2' MODIFIED PHENYLISOSERINE SIDE-CHAINS
    KANT, J
    HUANG, S
    WONG, H
    FAIRCHILD, C
    VYAS, D
    FARINA, V
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (11) : 2471 - 2474
  • [10] SYNTHESIS OF TAXOL FROM BACCATIN-3 VIA AN OXAZOLINE INTERMEDIATE
    KINGSTON, DGI
    CHAUDHARY, AG
    GUNATILAKA, AAL
    MIDDLETON, ML
    [J]. TETRAHEDRON LETTERS, 1994, 35 (26) : 4483 - 4484