Enantioselective Total Synthesis of (+)-Gliocladine C: Convergent Construction of Cyclotryptamine-Fused Polyoxopiperazines and a General Approach for Preparing Epidithiodioxopiperazines from Trioxopiperazine Precursors

被引：146

作者：

DeLorbe, John E. ^{[1
]}

Jabri, Salman Y. ^{[1
]}

Mennen, Steven M. ^{[1
]}

Overman, Larry E. ^{[1
]}

Zhang, Fang-Li ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 17期

关键词：

GLIOTOXIN; AGENT; INHIBITOR; INDUCTION; CHAETOCIN; OXIDATION; ANALOGS;

D O I：

10.1021/ja201789v

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A concise second-generation total synthesis of the fungal-derived alkaloid (+)-gliocladin C (11) in 10 steps and 1196 overall yield from isatin is reported. In addition, the epipolythiodioxopiperazine (ETP) natural product (+)-gliocladine C (6) has been prepared in six steps and 2996 yield from the di-(tert-butoxycarbonyl) precursor of 11. The total synthesis of 6 constitutes the first total synthesis of an ETP natural product containing a hydroxyl substituent adjacent to a quaternary carbon stereocenter in the pyrrolidine ring.

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页码：6549 / 6552

页数：4

相关论文

共 42 条

[1] SYNTHESIS OF 3-SUBSTITUTED INDOLES STARTING FROM ISATIN [J].

BERGMAN, J .

ACTA CHEMICA SCANDINAVICA, 1971, 25 (04) :1277-&

[2] 1H,1′H-[3,3′]biindolyl from the terrestrial fungus Gliocladium catenulatum [J].

Bertinetti, Brenda V. ;

Alejandra Rodriguez, M. ;

Godeas, Alicia M. ;

Cabrera, Gabriela M. .

JOURNAL OF ANTIBIOTICS, 2010, 63 (11) :681-683

[3] Direct Inhibition of Hypoxia-Inducible Transcription Factor Complex with Designed Dimeric Epidithiodiketopiperazine [J].

Block, Katherine M. ;

Wang, Hui ;

Szabo, Lajos Z. ;

Polaske, Nathan W. ;

Henchey, Laura K. ;

Dubey, Ramin ;

Kushal, Swati ;

Laszlo, Csaba F. ;

Makhoul, Joshua ;

Song, Zuohe ;

Meuillet, Emmanuelle J. ;

Olenyuk, Bogdan Z. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (50) :18078-18088

[4] Redox sensitive epidithiodioxopiperazines in biological mechanisms of toxicity [J].

Chai, CLL ;

Waring, P .

REDOX REPORT, 2000, 5 (05) :257-264

[5] Epidithiodiketopiperazines Block the Interaction between Hypoxia-inducible Factor-1α (HIF-1α) and p300 by a Zinc Ejection Mechanism [J].

Cook, Kristina M. ;

Hilton, Stephen T. ;

Mecinovic, Jasmin ;

Motherwell, William B. ;

Figg, William D. ;

Schofield, Christopher J. .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2009, 284 (39) :26831-26838

[6] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287

[7] A NEW APPROACH TO THE BICYCLIC HYDROXYLAMINE HEMIKETAL RING-SYSTEM OF ANTITUMOR-ANTIBIOTIC FR900482 VIA OXIDATIVE RING EXPANSION OF A TETRAHYDROPYRROLO[1,2-A]INDOLE [J].

DMITRIENKO, GI ;

DENHART, D ;

MITHANI, S ;

PRASAD, GKB ;

TAYLOR, NJ .

TETRAHEDRON LETTERS, 1992, 33 (39) :5705-5708

[8] Nematicidal epipolysulfanyldioxopiperazines from Gliocladium roseum [J].

Dong, JY ;

He, HP ;

Shen, YM ;

Zhang, KQ .

JOURNAL OF NATURAL PRODUCTS, 2005, 68 (10) :1510-1513

[9]

Erkel G, 2002, Z NATURFORSCH C, V57, P759

[10] TOTAL SYNTHESIS OF GLIOTOXIN [J].

FUKUYAMA, T ;

KISHI, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (21) :6723-6724

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