SYNTHETIC STRATEGY FOR THE COUPLING OF THE CALICHEAMICIN OLIGOSACCHARIDE WITH AGLYCONS - SYNTHESIS OF DYNEMICIN-A CALICHEAMICIN HYBRID STRUCTURES

被引：31

作者：

NICOLAOU, KC ^{[1
]}

SCHREINER, EP ^{[1
]}

STAHL, W ^{[1
]}

机构：

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1991年 / 30卷 / 05期

关键词：

D O I：

10.1002/anie.199105851

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An enediyne unit, an epoxide ring, and other functional groups characterize the aglycon moiety of 1. Compound 1 was synthesized stereoselectively by Schmidt coupling of the corresponding enediyne bridgehead alcohol after it had been converted into the hydroxyethyl compound by treatment with the trichloroacetimidate of the sugar moiety. The required reactions are tolerated by the highly sensitive functional groups in the molecule. This work brings the total synthesis of enediyne antibiotics one step closer. (Figure Presented.) Copyright © 1991 by VCH Verlagsgesellschaft mbH, Germany

引用

页码：585 / 588

页数：4

共 23 条

[1] BROMINOLYSIS REACTION OF STANNYLENE DERIVATIVES - REGIOSPECIFIC SYNTHESIS OF CARBOHYDRATE-DERIVED HYDROXY-KETONES
DAVID, S
THIEFFRY, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (06): : 1568 - 1573
[2] ESPERAMICINS, A NOVEL CLASS OF POTENT ANTITUMOR ANTIBIOTICS .2. STRUCTURE OF ESPERAMICIN-X
GOLIK, J
CLARDY, J
DUBAY, G
GROENEWOLD, G
KAWAGUCHI, H
KONISHI, M
KRISHNAN, B
OHKUMA, H
SAITOH, K
DOYLE, TW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (11) : 3461 - 3462
[3] ESPERAMICINS, A NOVEL CLASS OF POTENT ANTITUMOR ANTIBIOTICS .3. STRUCTURES OF ESPERAMICINS-A1, ESPERAMICIN-A2, AND ESPERAMICIN-A1B
GOLIK, J
DUBAY, G
GROENEWOLD, G
KAWAGUCHI, H
KONISHI, M
KRISHNAN, B
OHKUMA, H
SAITOH, K
DOYLE, TW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (11) : 3462 - 3464
[4] GRANDLER G, 1985, CARBOHYD RES, V135, P203
[5] DYNEMICIN A, A NOVEL ANTIBIOTIC WITH THE ANTHRAQUINONE AND 1,5-DIYN-3-ENE SUBUNIT
KONISHI, M
OHKUMA, H
MATSUMOTO, K
TSUNO, T
KAMEI, H
MIYAKI, T
OKI, T
KAWAGUCHI, H
VANDUYNE, GD
CLARDY, J
[J]. JOURNAL OF ANTIBIOTICS, 1989, 42 (09) : 1449 - 1452
[6] CRYSTAL AND MOLECULAR-STRUCTURE OF DYNEMICIN-A - A NOVEL 1,5-DIYN-3-ENE ANTITUMOR ANTIBIOTIC
KONISHI, M
OHKUMA, H
TSUNO, T
OKI, T
VANDUYNE, GD
CLARDY, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (09) : 3715 - 3716
[7] CALICHEMICINS, A NOVEL FAMILY OF ANTITUMOR ANTIBIOTICS .1. CHEMISTRY AND PARTIAL STRUCTURE OF CALICHEMICIN-GAMMA-1
LEE, MD
DUNNE, TS
SIEGEL, MM
CHANG, CC
MORTON, GO
BORDERS, DB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (11) : 3464 - 3466
[8] CALICHEMICINS, A NOVEL FAMILY OF ANTITUMOR ANTIBIOTICS .2. CHEMISTRY AND STRUCTURE OF CALICHEMICIN-GAMMA-1
LEE, MD
DUNNE, TS
CHANG, CC
ELLESTAD, GA
SIEGEL, MM
MORTON, GO
MCGAHREN, WJ
BORDERS, DB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (11) : 3466 - 3468
[9] AN EFFICIENT METHOD FOR GLUCOSYLATION OF HYDROXY COMPOUNDS USING GLUCOPYRANOSYL FLUORIDE
MUKAIYAMA, T
MURAI, Y
SHODA, S
[J]. CHEMISTRY LETTERS, 1981, (03) : 431 - 432
[10] SYNTHESIS OF DYNEMICIN-A MODELS
NICOLAOU, KC
HWANG, CK
SMITH, AL
WENDEBORN, SV
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (20) : 7416 - 7418

← 1 2 3 →