Use of a Tandem Prins/Friedel-Crafts Reaction in the Construction of the Indeno-Tetrahydropyridine Core of the Haouamine Alkaloids: Formal Synthesis of (-)-Haouamine A

被引：50

作者：

Fenster, Erik ^{[1
]}

Fehl, Charlie ^{[1
]}

Aube, Jeffrey ^{[1
]}

机构：

[1] Univ Kansas, KU Chem Methodol & Lib Dev Ctr, Lawrence, KS 66047 USA

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 10期

关键词：

3-COMPONENT SYNTHESIS; ONE-POT; CYCLIZATION;

D O I：

10.1021/ol200725m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A tandem Prins/friedel-Crafts reaction useful for the construction of the indeno-tetrahydropyridine core of the haouamine alkaloids and a formal synthesis of (-)-haouamine A are described.

引用

页码：2614 / 2617

页数：4

共 21 条

[1] Total synthesis of (±)-haouamine A [J].

Baran, PS ;

Burns, NZ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (12) :3908-3909

[2] Simple and one-pot protocol for synthesis of indene-spiro-oxindoles involving tandem Prins and Friedel-Crafts reactions [J].

Basavaiah, Deevi ;

Reddy, Kanumuri Ramesh .

ORGANIC LETTERS, 2007, 9 (01) :56-60

[3] On the origin of the haouamine alkaloids [J].

Burns, Noah Z. ;

Baran, Phil S. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (01) :205-208

[4] Scalable Total Synthesis and Biological Evaluation of Haouamine A and Its Atropisomer [J].

Burns, Noah Z. ;

Krylova, Irina N. ;

Hannoush, Rami N. ;

Baran, Phil S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (26) :9172-+

[5] Formal total synthesis of (-)-haouamine A [J].

Fuerstner, Alois ;

Ackerstaff, Jens .

CHEMICAL COMMUNICATIONS, 2008, (25) :2870-2872

[6] Haouamines A and B:: A new class of alkaloids from the ascidian Aplidium haouarianum [J].

Garrido, L ;

Zubía, E ;

Ortega, MJ ;

Salvá, J .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (02) :293-299

[7] Synthetic studies toward the haouamines [J].

Grundl, MA ;

Trauner, D .

ORGANIC LETTERS, 2006, 8 (01) :23-25

[8] Formal total synthesis of the cytotoxic marine ascidian alkaloid haouamine A [J].

Jeong, Jeannie H. ;

Weinreb, Steven M. .

ORGANIC LETTERS, 2006, 8 (11) :2309-2312

[9] Negishi cross-coupling reactions of α-amino acid-derived organozinc reagents and aromatic bromides [J].

Oswald, Claire L. ;

Carrillo-Marquez, Tomas ;

Caggiano, Lorenzo ;

Jackson, Richard F. W. .

TETRAHEDRON, 2008, 64 (04) :681-687

[10] Stereoselective One-Pot, Three-Component Synthesis of 4-Aryltetrahydropyran via Prins-Friedel-Crafts Reaction [J].

Reddy, U. C. ;

Bondalapati, S. ;

Saikia, Anil K. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (06) :2605-2608

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