Total synthesis of (+)-batzelladine A and (-)-batzelladine D via [4+2]-annulation of vinyl carbodiimides with N-alkyl imines

被引：89

作者：

Arnold, Michael A.

Day, Kenneth A.

Duron, Sergio G.

Gin, David Y.

机构：

[1] Mem Sloan Kettering Canc Ctr, Mol Pharmacol & Chem Program, New York, NY 10021 USA

[2] Univ Illinois, Dept Chem, Urbana, IL 61801 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 40期

关键词：

D O I：

10.1021/ja063860+

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A diastereoselective [4 + 2]-annulation of vinyl carbodiimides with chiral N-alkyl imines has been developed to access the stereochemically rich polycyclic guanidine cores of the batzelladine alkaloids. Application of this strategy, together with additional key steps such as long-range directed hydrogenation and diastereoselective intramolecular iodo-amination, led to highly convergent total syntheses of (-)-batzelladine D and (+)- batzelladine A with excellent stereocontrol.

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收藏

页码：13255 / 13260

页数：6

相关论文

共 40 条

[1] Diastereoselective [4+2] annulation of vinyl carbodiimides with N-alkyl imines.: Asymmetric synthetic access to the batzelladine alkaloids [J].

Arnold, MA ;

Durón, SG ;

Gin, DY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (19) :6924-6925

[2] Synthesis of the left hand unit of batzelladine F; Revision of the reported relative stereochemistry [J].

Black, GP ;

Murphy, PJ ;

Thornhill, AJ ;

Walshe, NDA ;

Zanetti, C .

TETRAHEDRON, 1999, 55 (21) :6547-6554

[3] A short synthetic route to the tricyclic guanidinium core of the batzelladine alkaloids [J].

Black, GP ;

Murphy, PJ ;

Walshe, NDA ;

Hibbs, DE ;

Hursthouse, MB ;

Malik, KMA .

TETRAHEDRON LETTERS, 1996, 37 (38) :6943-6946

[4] A short synthetic route to the tricyclic guanidinium core of the batzelladine alkaloids [J].

Black, GP ;

Murphy, PJ ;

Walshe, NDA .

TETRAHEDRON, 1998, 54 (32) :9481-9488

[5] Novel polycyclic guanidine alkaloids from two marine sponges of the genus Monanchora [J].

Braekman, JC ;

Daloze, D ;

Tavares, R ;

Hajdu, E ;

Van Soest, RWM .

JOURNAL OF NATURAL PRODUCTS, 2000, 63 (02) :193-196

[6] Evolution of a strategy for the synthesis of structurally complex batzelladine alkaloids. Enantioselective total synthesis of the proposed structure of batzelladine F and structural revision [J].

Cohen, F ;

Overman, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (08) :2594-2603

[7] Enantioselective total synthesis of batzelladine F and definition of its structure [J].

Cohen, F ;

Overman, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (08) :2604-2608

[8] Enantioselective total synthesis of batzelladine F: Structural revision and stereochemical definition [J].

Cohen, F ;

Overman, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (43) :10782-10783

[9] Asymmetric total synthesis of batzelladine D [J].

Cohen, F ;

Overman, LE ;

Sakata, SKL .

ORGANIC LETTERS, 1999, 1 (13) :2169-2172

[10] DIRECTING EFFECTS IN HOMOGENEOUS HYDROGENATION WITH [IR(COD)(PCY3)(PY)]PF6 [J].

CRABTREE, RH ;

DAVIS, MW .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (14) :2655-2661

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