TOTAL SYNTHESIS OF (+/-)-DYNEMICIN-A

被引：70

作者：

SHAIR, MD ^{[1
]}

YOON, TY ^{[1
]}

DANISHEFSKY, SJ ^{[1
]}

机构：

[1] SLOAN KETTERING INST CANC RES,BIOORGAN CHEM LAB,NEW YORK,NY 10021

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1995年 / 34卷 / 16期

关键词：

ANTHRAQUINONES; DYNEMICIN A; ENEDIYNES; TOTAL SYNTHESES;

D O I：

10.1002/anie.199517211

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Pivotal steps in the total synthesis of the enediyne antibiotic dynemicin A are (1) a palladium‐mediated double cross‐coupling reaction to construct the enediyne array, and (2) cycloaddition of a quinone imine with the anion of a suitably protected homophthalic anhydride followed by oxidation in air to fashion the anthraquinone moiety. (Figure Presented.) Copyright © 1995 by VCH Verlagsgesellschaft mbH, Germany

引用

页码：1721 / 1723

页数：3

共 25 条

[1] OXIDATION AND REDUCTION OF SOME METHOXY-ANTHRACENES AND THEIR DERIVATIVES [J].

CAMERON, DW ;

SCHUTZ, PE .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (21) :2121-&

[2]

Guyot M., 1973, TETRAHEDRON LETT, V14, P3433

[3]

HITCHCOCK SA, 1994, ANGEW CHEM INT EDIT, V33, P858, DOI 10.1002/anie.199408581

[4]

HITCHCOCK SA, 1994, ANGEW CHEM, V106, P928

[5] CONJUGATED SYSTEMS IN THE ANTHRACENE SERIES .4. TRANSANNULAR ANTHRANOL PEROXIDES [J].

JULIAN, PL ;

COLE, W ;

DIEMER, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1945, 67 (10) :1721-1723

[6] TOTAL SYNTHESIS OF DL-INDOLIZOMYCIN [J].

KIM, G ;

CHUMOYER, MY ;

DANISHEFSKY, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (05) :2003-2005

[7] FACILE AND EFFICIENT SYNTHESES OF CARBOXYLIC ANHYDRIDES AND AMIDES USING (TRIMETHYLSILYL)ETHOXYACETYLENE [J].

KITA, Y ;

AKAI, S ;

AJIMURA, N ;

YOSHIGI, M ;

TSUGOSHI, T ;

YASUDA, H ;

TAMURA, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (22) :4150-4158

[8] 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

[9] THE DYNEMICIN DNA INTERCALATION COMPLEX - A MODEL BASED ON DNA AFFINITY CLEAVAGE AND MOLECULAR-DYNAMICS SIMULATION [J].

LANGLEY, DR ;

DOYLE, TW ;

BEVERIDGE, DL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (12) :4395-4403

[10] HIGHLY CONVERGENT ROUTE TO DYNEMICINS OF WIDE STRUCTURAL VARIABILITY - ENANTIOSELECTIVE SYNTHESIS OF QUINONE IMINE PRECURSORS TO NATURAL AND NONNATURAL DYNEMICINS [J].

MYERS, AG ;

FRALEY, ME ;

TOM, NJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (25) :11556-11557

← 1 2 3 →