Studies Toward Communesin F: A Diels-Alder Approach

被引：25

作者：

Danielsson, Jakob ^{[1
]}

Somfai, Peter ^{[1
,2
]}

机构：

[1] Lund Univ, Dept Chem, Ctr Anal & Synth, S-22100 Lund, Sweden

[2] Univ Tartu, Inst Technol, EE-50411 Tartu, Estonia

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 03期

关键词：

BIOMIMETIC APPROACH; CONSTRUCTION; PEROPHORAMIDINE; ALKALOIDS;

D O I：

10.1021/ol403516s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Diels-Alder reaction is used as a key step in a synthetic study toward communesin F, in order to simultaneously introduce both of the all-carbon quaternary stereocenters with complete control of relative stereochemistry. Further manipulations of the cycloadduct, toward the hexacyclic core-structure of communesin F, are also disclosed.

引用

页码：784 / 787

页数：4

共 37 条

[31] Isolation, structure determination, and biological activity of a novel alkaloid, perophoramidine, from the Philippine ascidian Perophora namei [J].

Verbitski, SM ;

Mayne, CL ;

Davis, RA ;

Concepcion, GP ;

Ireland, CM .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) :7124-7126

[32] Total Synthesis of (+)-Perophoramidine and Determination of the Absolute Configuration [J].

Wu, Haoxing ;

Xue, Fei ;

Xiao, Xue ;

Qin, Yong .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (40) :14052-14054

[33] Biomimetic approach to perophoramidine and communesin via an intramolecular cyclopropanation reaction [J].

Yang, J ;

Song, H ;

Xiao, X ;

Wang, J ;

Qin, Y .

ORGANIC LETTERS, 2006, 8 (10) :2187-2190

[34] Total synthesis of (±)-communesin F [J].

Yang, Jun ;

Wu, Haoxing ;

Shen, Liquin ;

Qin, Yong .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (45) :13794-+

[35] Construction of Vicinal All-Carbon Quaternary Stereocenters by Catalytic Asymmetric Alkylation Reaction of 3-Bromooxindoles with 3-Substituted Indoles: Total Synthesis of (+)-Perophoramidine [J].

Zhang, Hailong ;

Hong, Liang ;

Kang, Hong ;

Wang, Rui .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (38) :14098-14101

[36] Enantioselective Total Syntheses of Communesins A and B [J].

Zuo, Zhiwei ;

Ma, Dawei .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (50) :12008-12011

[37] Total Synthesis and Absolute Stereochemical Assignment of (-)-Communesin F [J].

Zuo, Zhiwei ;

Xie, Weiqing ;

Ma, Dawei .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (38) :13226-13228

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