SYNTHESIS OF THE CALICHEAMICIN ARYLTETRASACCHARIDE DOMAIN BEARING A REDUCING TERMINUS - COUPLING OF FULLY SYNTHETIC AGLYCONE AND CARBOHYDRATE DOMAINS BY THE SCHMIDT REACTION

被引:49
作者
HALCOMB, RL [1 ]
BOYER, SH [1 ]
DANISHEFSKY, SJ [1 ]
机构
[1] YALE UNIV,DEPT CHEM,225 PROSPECT ST,NEW HAVEN,CT 06511
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1992年 / 31卷 / 03期
关键词
D O I
10.1002/anie.199203381
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The successful coupling of two building blocks constructed by total synthesis is described here as a route to calicheamicin (1). The aryltetrasaccharide section of 1 is shown for the first time to function as a glycosyl donor for aglycone intermediates.
引用
收藏
页码:338 / 340
页数:3
相关论文
共 53 条
  • [1] AIYAR J, UNPUB
  • [2] REACTIVE 1,4-DEHYDROAROMATICS
    BERGMAN, RG
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1973, 6 (01) : 25 - 31
  • [3] BORCH RF, 1972, ORG SYNTH, V52, P124
  • [4] TOTAL SYNTHESIS OF RACEMIC SESBANINE
    BOTTARO, JC
    BERCHTOLD, GA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (06) : 1176 - 1176
  • [5] CONCERNING 1,5-DIDEHYDRO[10]ANNULENE SYSTEM
    DARBY, N
    KIM, CU
    SALAUN, JA
    SHELTON, KW
    TAKADA, S
    MASAMUNE, S
    [J]. JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (23): : 1516 - &
  • [6] REGIOSELECTIVE MANIPULATION OF HYDROXYL-GROUPS VIA ORGANOTIN DERIVATIVES
    DAVID, S
    HANESSIAN, S
    [J]. TETRAHEDRON, 1985, 41 (04) : 643 - 663
  • [7] READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES
    DESS, DB
    MARTIN, JC
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) : 4155 - 4156
  • [8] SITE-SPECIFIC ATOM TRANSFER FROM DNA TO A BOUND LIGAND DEFINES THE GEOMETRY OF A DNA CALICHEAMICIN GAMMA-1I COMPLEX
    DEVOSS, JJ
    TOWNSEND, CA
    DING, WD
    MORTON, GO
    ELLESTAD, GA
    ZEIN, N
    TABOR, AB
    SCHREIBER, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (26) : 9669 - 9670
  • [9] THE CARBOHYDRATE DOMAIN OF CALICHEAMICIN GAMMA-1(I) DETERMINES ITS SEQUENCE SPECIFICITY FOR DNA CLEAVAGE
    DRAK, J
    IWASAWA, N
    DANISHEFSKY, S
    CROTHERS, DM
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1991, 88 (17) : 7464 - 7468
  • [10] THE STRUCTURE OF NEOCARZINOSTATIN CHROMOPHORE POSSESSING A NOVEL BICYCLO-[7,3,0]DODECADIYNE SYSTEM
    EDO, K
    MIZUGAKI, M
    KOIDE, Y
    SETO, H
    FURIHATA, K
    OTAKE, N
    ISHIDA, N
    [J]. TETRAHEDRON LETTERS, 1985, 26 (03) : 331 - 334