TOTAL SYNTHESIS OF CALICHEAMICIN DYNEMICIN HYBRID MOLECULES

被引：44

作者：

NICOLAOU, KC ^{[1
]}

SCHREINER, EP ^{[1
]}

IWABUCHI, Y ^{[1
]}

SUZUKI, T ^{[1
]}

机构：

[1] UNIV CALIF SAN DIEGO, DEPT CHEM, LA JOLLA, CA 92093 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1992年 / 31卷 / 03期

关键词：

D O I：

10.1002/anie.199203401

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Synthetic enediyne cytostatics/antibiotics are the goal of the preparative work described here. Of the four isomeric calicheamicin‐dynemicin hybrid compounds obtained, only those with the same configuration as calicheamin at all stereocenters are cytostatically active. One of the active isomers is 1. (Figure Presented.) Copyright © 1992 by VCH Verlagsgesellschaft mbH, Germany

引用

页码：340 / 342

页数：3

共 19 条

[1]

DOI T, 1991, J ORG CHEM, V56, P3465, DOI 10.1021/jo00011a002

[2] TOTAL SYNTHESIS OF CALICHEAMICINONE - NEW ARRANGEMENTS FOR ACTUATION OF THE REDUCTIVE CYCLOAROMATIZATION OF AGLYCON CONGENERS [J].

HASELTINE, JN ;

CABAL, MP ;

MANTLO, NB ;

IWASAWA, N ;

YAMASHITA, DS ;

COLEMAN, RS ;

DANISHEFSKY, SJ ;

SCHULTE, GK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (10) :3850-3866

[3] THE 10-MEMBERED RING ANALOGS OF NEOCARZINOSTATIN CHROMOPHORE - DESIGN, SYNTHESIS, AND MODE OF DECOMPOSITION [J].

HIRAMA, M ;

FUJIWARA, K ;

SHIGEMATU, K ;

FUKAZAWA, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (11) :4120-4122

[4] DYNEMICIN A, A NOVEL ANTIBIOTIC WITH THE ANTHRAQUINONE AND 1,5-DIYN-3-ENE SUBUNIT [J].

KONISHI, M ;

OHKUMA, H ;

MATSUMOTO, K ;

TSUNO, T ;

KAMEI, H ;

MIYAKI, T ;

OKI, T ;

KAWAGUCHI, H ;

VANDUYNE, GD ;

CLARDY, J .

JOURNAL OF ANTIBIOTICS, 1989, 42 (09) :1449-1452

[5] CRYSTAL AND MOLECULAR-STRUCTURE OF DYNEMICIN-A - A NOVEL 1,5-DIYN-3-ENE ANTITUMOR ANTIBIOTIC [J].

KONISHI, M ;

OHKUMA, H ;

TSUNO, T ;

OKI, T ;

VANDUYNE, GD ;

CLARDY, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (09) :3715-3716

[6] CALICHEMICINS, A NOVEL FAMILY OF ANTITUMOR ANTIBIOTICS .1. CHEMISTRY AND PARTIAL STRUCTURE OF CALICHEMICIN-GAMMA-1 [J].

LEE, MD ;

DUNNE, TS ;

SIEGEL, MM ;

CHANG, CC ;

MORTON, GO ;

BORDERS, DB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (11) :3464-3466

[7] CALICHEMICINS, A NOVEL FAMILY OF ANTITUMOR ANTIBIOTICS .2. CHEMISTRY AND STRUCTURE OF CALICHEMICIN-GAMMA-1 [J].

LEE, MD ;

DUNNE, TS ;

CHANG, CC ;

ELLESTAD, GA ;

SIEGEL, MM ;

MORTON, GO ;

MCGAHREN, WJ ;

BORDERS, DB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (11) :3466-3468

[8]

MAGNUS P, 1991, J CHEM SOC CHEM COMM, P554

[9] ENANTIOSELECTIVE SYNTHESIS OF THE EPOXY DIYNE CORE OF NEOCARZINOSTATIN CHROMOPHORE [J].

MYERS, AG ;

HARRINGTON, PM ;

KUO, EY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :694-695

[10] SYNTHETIC STRATEGY FOR THE COUPLING OF THE CALICHEAMICIN OLIGOSACCHARIDE WITH AGLYCONS - SYNTHESIS OF DYNEMICIN-A CALICHEAMICIN HYBRID STRUCTURES [J].

NICOLAOU, KC ;

SCHREINER, EP ;

STAHL, W .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (05) :585-588

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