Total Syntheses of Tardioxopiperazine A, Isoechinulin A, and Variecolorin C

被引：33

作者：

Dai, Qipu ^{[1
]}

Xie, Xingang ^{[1
]}

Xu, Shiyan ^{[1
]}

Ma, Donghui ^{[1
]}

Tang, Shibing ^{[1
]}

She, Xuegong ^{[1
,2
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Dept Chem, Lanzhou 730000, Peoples R China

[2] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 09期

关键词：

CROSS-COUPLING REACTIONS; STEREOSELECTIVE SYNTHESIS; FUNGUS ASPERGILLUS; ALKENYL HALIDES; PALLADIUM; CHLORIDES; TOSYLATES; ALKALOIDS; OLEFINS;

D O I：

10.1021/ol2005616

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

First total syntheses of the isoechinulin-type alkaloids: Tardioxopiperazine A, Isoechinulin A, and Variecolorin C have been achieved from a common key intermediate 5, which was derived from a regiocontrolled Stille cross-coupling reaction of an allylindium reagent.

引用

页码：2302 / 2305

页数：4

共 30 条

[1] NOVEL STEREOSPECIFIC ALKENYL-ALKENYL CROSS-COUPLING BY A PALLADIUM-CATALYZED OR NICKEL-CATALYZED REACTION OF ALKENYLALANES WITH ALKENYL HALIDES [J].

BABA, S ;

NEGISHI, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (21) :6729-6731

[2] Enantioselective total synthesis of avrainvillamide and the stephacidins [J].

Baran, Phil S. ;

Hafensteiner, Benjamin D. ;

Ambhaikar, Narendra B. ;

Guerrero, Carlos A. ;

Gallagher, John D. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (26) :8678-8693

[3] Isolation of Putative Biosynthetic Intermediates of Prenylated Indole Alkaloids from a Thermophilic Fungus Talaromyces thermophilus [J].

Chu, Yan-Sheng ;

Niu, Xue-Mei ;

Wang, Yan-Li ;

Guo, Ji-Peng ;

Pan, Wen-Zheng ;

Huang, Xiao-Wei ;

Zhang, Ke-Qin .

ORGANIC LETTERS, 2010, 12 (19) :4356-4359

[4]

Corriu R.J. P., 1972, J. Chem. Soc. Chem. Commun, P144

[5] PALLADIUM-CATALYZED COUPLING OF ARYL TRIFLATES WITH ORGANOSTANNANES [J].

ECHAVARREN, AM ;

STILLE, JK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5478-5486

[6]

Fujimoto K, 1999, CHEM PHARM BULL, V47, P1426

[7]

Fürstner A, 2002, ANGEW CHEM INT EDIT, V41, P609

[8] Ecology and taxonomy of pathogenic Aspergilli [J].

Gugnani, HC .

FRONTIERS IN BIOSCIENCE-LANDMARK, 2003, 8 :S346-S357

[9] Cytotoxic and other metabolites of Aspergillus inhabiting the rhizosphere of Sonoran desert plants [J].

He, J ;

Wijeratne, EMK ;

Bashyal, BP ;

Zhan, JX ;

Seliga, CJ ;

Liu, MPX ;

Pierson, EE ;

Pierson, LS ;

VanEtten, HD ;

Gunatilaka, AAL .

JOURNAL OF NATURAL PRODUCTS, 2004, 67 (12) :1985-1991

[10]

HENTGES SG, 1980, J AM CHEM SOC, V102, P4263, DOI 10.1021/ja00532a050

← 1 2 3 →