Studies Toward Communesin F: A Diels-Alder Approach

被引：24

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

[1] An approach to the total synthesis of the marine ascidian metabolite perophoramidine via a halogen-selective tandem Heck/carbonylation strategy [J].

Artman, GD ;

Weinreb, SM .

ORGANIC LETTERS, 2003, 5 (09) :1523-1526

[2] Total Synthesis of (±)-Communesin F via a Cycloaddition with Indol-2-one [J].

Belmar, Johannes ;

Funk, Raymond L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (41) :16941-16943

[3] Stereoselective construction of quaternary stereocenters [J].

Christoffers, J ;

Baro, A .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) :1473-1482

[4]

Christoffers J, 2005, QUATERNARY STEREOCENTERS: CHALLENGES AND SOLUTIONS FOR ORGANIC SYNTHESIS, P1, DOI 10.1002/3527606858

[5]

Christoffers J, 2001, ANGEW CHEM INT EDIT, V40, P4591, DOI 10.1002/1521-3773(20011217)40:24<4591::AID-ANIE4591>3.0.CO

[6]

2-V

[7] Generation of aza-ortho-xylylenes via ring opening of 2-(2-acylaminophenyl)aziridines:: Application in the construction of the communesin ring system [J].

Crawley, Seth L. ;

Funk, Raymond L. .

ORGANIC LETTERS, 2006, 8 (18) :3995-3998

[8] A synthetic approach to nomofungin/communesin B [J].

Crawley, SL ;

Funk, RL .

ORGANIC LETTERS, 2003, 5 (18) :3169-3171

[9] Communesins G and H, new alkaloids from the psychrotolerant fungus Penicillium rivulum [J].

Dalsgaard, PW ;

Blunt, JW ;

Munro, MHG ;

Frisvad, JC ;

Christophersen, C .

JOURNAL OF NATURAL PRODUCTS, 2005, 68 (02) :258-261

[10] Catalytic asymmetric synthesis of all-carbon quaternary stereocenters [J].

Douglas, CJ ;

Overman, LE .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) :5363-5367

← 1 2 3 4 →