A biogenetically-inspired synthesis of a ring-D model of kinamycin F:: Insights into the conformation of ring D

被引：20

作者：

Chen, Nan ^{[1
]}

Carriere, Marjolaine B. ^{[1
]}

Laufer, Radoslaw S. ^{[1
]}

Taylor, Nicholas J. ^{[1
]}

Dmitrienko, Gary I. ^{[1
]}

机构：

[1] Univ Waterloo, Dept Chem, Waterloo, ON N2L 3G1, Canada

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 03期

关键词：

D O I：

10.1021/ol702650u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient three-step construction of the highly oxygenated D-ring of the kinamycin antibiotics is reported for a simple model system. A comparison of the spectroscopic characteristics of the synthetic models with those of natural kinamycin F, which is suspected to be the bioactive form of the kinamycins, leads to the conclusion that the favored D-ring conformation of kinamycin F differs from that of the other partially or fully acylated variants.

引用

页码：381 / 384

页数：4

共 29 条

[1]

Akira K, 1998, DRUG METAB DISPOS, V26, P457

[2] Benzo[b]fluorenes via indanone dianion annulation.: A short synthesis of prekinamycin [J].

Birman, Vladimir B. ;

Zhao, Zhufeng ;

Guo, Lei .

ORGANIC LETTERS, 2007, 9 (07) :1223-1225

[3] TI(O-I-PR)4-MEDIATED NUCLEOPHILIC OPENINGS OF 2,3-EPOXY ALCOHOLS - A MILD PROCEDURE FOR REGIOSELECTIVE RING-OPENING [J].

CARON, M ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) :1557-1560

[4] Studies on the mechanism of action of prekinamycin, a member of the diazoparaquinone family of natural products:: Evidence for both sp2 radical and orthoquinonemethide intermediates [J].

Feldman, Ken S. ;

Eastman, Kyle J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (38) :12562-12573

[5]

FURUSAKI A, 1972, ISRAEL J CHEM, V10, P173

[6] Identification of prekinamycin in extracts of Streptomyces murayamaensis [J].

Gould, SJ ;

Chen, J ;

Cone, MC ;

Gore, MP ;

Melville, CR ;

Tamayo, N .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (17) :5720-5721

[7] Biosynthesis of the kinamycins [J].

Gould, SJ .

CHEMICAL REVIEWS, 1997, 97 (07) :2499-2509

[8] REVISED STRUCTURES FOR THE KINAMYCIN ANTIBIOTICS - 5-DIAZOBENZO[B]FLUORENES RATHER THAN BENZO[B]CARBAZOLE CYANAMIDES [J].

GOULD, SJ ;

TAMAYO, N ;

MELVILLE, CR ;

CONE, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (05) :2207-2208

[9] Kinamycins A and C, bacterial metabolites that contain an unusual diazo group, as potential new anticancer agents: antiproliferative and cell cycle effects [J].

Hasinoff, Brian B. ;

Wu, Xing ;

Yalowich, Jack C. ;

Goodfellow, Valerie ;

Laufer, Radoslaw S. ;

Adedayo, Otunola ;

Dmitrienko, Gary I. .

ANTI-CANCER DRUGS, 2006, 17 (07) :825-837

[10] Total synthesis of the structure proposed for prekinamycin [J].

Hauser, FM ;

Zhou, MT .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (17) :5722-5722

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