Synthesis of taxoids 3.: A novel and efficient method for preparation of taxoids by employing cis-glycidic acid.

被引:25
作者
Yamaguchi, T [1 ]
Harada, N [1 ]
Ozaki, K [1 ]
Hashiyama, T [1 ]
机构
[1] Tanabe Seiyaku Co Ltd, Med Chem Res Lab, Toda, Saitama 3358505, Japan
关键词
taxoids; stereocontrol; epoxides; esterification;
D O I
10.1016/S0040-4039(98)01124-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel route for the synthesis of docetaxel (2) using esterification of (2R,3R)glycidic acid with 7, 10-bis-O-(2,2,2-trichloroethoxycarbonyl)-10-deacetylbaccatin III is described. Subsequent stereo- and regio-selective conversion afforded 2 and related novel compounds. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5575 / 5578
页数:4
相关论文
共 25 条
  • [1] REGIOCHEMICAL CONTROL OF THE RING-OPENING OF 1,2-EPOXIDES BY MEANS OF CHELATING PROCESSES .11. RING-OPENING REACTIONS OF ALIPHATIC MONOFUNCTIONALIZED AND DIFUNCTIONALIZED CIS AND TRANS 2,3-EPOXY AND 3,4-EPOXY ESTERS
    AZZENA, F
    CROTTI, P
    FAVERO, L
    PINESCHI, M
    [J]. TETRAHEDRON, 1995, 51 (48) : 13409 - 13422
  • [2] IMPROVED PROTECTION AND ESTERIFICATION OF A PRECURSOR OF THE TAXOTERE(R) AND TAXOL SIDE-CHAINS
    COMMERCON, A
    BEZARD, D
    BERNARD, F
    BOURZAT, JD
    [J]. TETRAHEDRON LETTERS, 1992, 33 (36) : 5185 - 5188
  • [3] AN IMPROVED PROCEDURE FOR THE PREPARATION OF 1-BENZYL-1H-1,2,3-TRIAZOLES FROM BENZYL AZIDES
    COTTRELL, IF
    HANDS, D
    HOUGHTON, PG
    HUMPHREY, GR
    WRIGHT, SHB
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1991, 28 (02) : 301 - 304
  • [4] 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
  • [5] SELECTIVE TRANSFORMATIONS OF THREO-2,3-DIHYDROXY ESTERS
    FLEMING, PR
    SHARPLESS, KB
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) : 2869 - 2875
  • [6] Taxol semisynthesis: A highly enantio- and diastereoselective synthesis of the side chain and a new method for ester formation at C-13 using thioesters
    Gennari, C
    Carcano, M
    Donghi, M
    Mongelli, N
    Vanotti, E
    Vulpetti, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (14) : 4746 - 4755
  • [7] GEORG GI, 1995, ACS SYM SER, V583, P31
  • [8] RELATIONSHIPS BETWEEN THE STRUCTURE OF TAXOL ANALOGS AND THEIR ANTIMITOTIC ACTIVITY
    GUERITTEVOEGELEIN, F
    GUENARD, D
    LAVELLE, F
    LEGOFF, MT
    MANGATAL, L
    POTIER, P
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (03) : 992 - 998
  • [9] CHEMICAL STUDIES OF 10-DEACETYL BACCATIN .3. HEMISYNTHESIS OF TAXOL DERIVATIVES
    GUERITTEVOEGELEIN, F
    SENILH, V
    DAVID, B
    GUENARD, D
    POTIER, P
    [J]. TETRAHEDRON, 1986, 42 (16) : 4451 - 4460
  • [10] Harada N, 1997, HETEROCYCLES, V44, P305