SYNTHESIS AND CHEMISTRY OF DYNEMICIN-A MODELS

被引：112

作者：

NICOLAOU, KC ^{[1
]}

SMITH, AL ^{[1
]}

WENDEBORN, SV ^{[1
]}

HWANG, CK ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1991年 / 113卷 / 08期

关键词：

D O I：

10.1021/ja00008a045

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of the model systems 10 and 22 of dynemicin A (2) containing the nitrogen, enediyne, and epoxide functionalities has been achieved. These models are shown to undergo acid-induced triggering to give the corresponding Bergman-cyclized products in the presence of suitable H atom donors. Removal of the N protecting group from 22 gave the unstable free amine 30, which was shown to cause double-stranded-DNA cleavage, presumably in a manner similar to that of dynemicin A (2) itself. Some interesting chemistry related to dicobalt complexes of the enediynes is also presented.

引用

页码：3106 / 3114

页数：9

共 41 条

[1] REACTIVE 1,4-DEHYDROAROMATICS [J].

BERGMAN, RG .

ACCOUNTS OF CHEMICAL RESEARCH, 1973, 6 (01) :25-31

[2] REARRANGEMENTS OF N-OXIDES - A NOVEL SYNTHESIS OF PYRIDYL CARBINOLS AND ALDEHYDES [J].

BOEKELHEIDE, V ;

LINN, WJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (05) :1286-1291

[3] TOTAL SYNTHESIS OF CALICHEAMICINONE - A SOLUTION TO THE PROBLEM OF THE ELUSIVE URETHANE [J].

CABAL, MP ;

COLEMAN, RS ;

DANISHEFSKY, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (08) :3253-3255

[4] SYNTHESIS AND SYNTHETIC UTILITY OF 1-ACYL-5-(TRIALKYLSILYL)-1,2-DIHYDROPYRIDINES - SYNTHESIS OF (+/-)-ELAEOKANINE-A [J].

COMINS, DL ;

MYOUNG, YC .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) :292-298

[5] CYCLODEHYDRATION OF ORTHO-VINYL ANILIDES - A GENERAL-SYNTHESIS OF SUBSTITUTED QUINOLINES [J].

CURRAN, DP ;

KUO, SC .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (11) :2063-2065

[6] CONCERNING 1,5-DIDEHYDRO[10]ANNULENE SYSTEM [J].

DARBY, N ;

KIM, CU ;

SALAUN, JA ;

SHELTON, KW ;

TAKADA, S ;

MASAMUNE, S .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (23) :1516-&

[7] THE STRUCTURE OF NEOCARZINOSTATIN CHROMOPHORE POSSESSING A NOVEL BICYCLO-[7,3,0]DODECADIYNE SYSTEM [J].

EDO, K ;

MIZUGAKI, M ;

KOIDE, Y ;

SETO, H ;

FURIHATA, K ;

OTAKE, N ;

ISHIDA, N .

TETRAHEDRON LETTERS, 1985, 26 (03) :331-334

[8] ESPERAMICINS, A NOVEL CLASS OF POTENT ANTITUMOR ANTIBIOTICS .2. STRUCTURE OF ESPERAMICIN-X [J].

GOLIK, J ;

CLARDY, J ;

DUBAY, G ;

GROENEWOLD, G ;

KAWAGUCHI, H ;

KONISHI, M ;

KRISHNAN, B ;

OHKUMA, H ;

SAITOH, K ;

DOYLE, TW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (11) :3461-3462

[9] ESPERAMICINS, A NOVEL CLASS OF POTENT ANTITUMOR ANTIBIOTICS .3. STRUCTURES OF ESPERAMICINS-A1, ESPERAMICIN-A2, AND ESPERAMICIN-A1B [J].

GOLIK, J ;

DUBAY, G ;

GROENEWOLD, G ;

KAWAGUCHI, H ;

KONISHI, M ;

KRISHNAN, B ;

OHKUMA, H ;

SAITOH, K ;

DOYLE, TW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (11) :3462-3464

[10]

GREENE TW, 1981, PROTECTIVE GROUPS OR

← 1 2 3 4 5 →