A New Approach to Highly Substituted Cyclopentanoids from a Concise Formal Synthesis of (+)-Roseophilin

被引：26

作者：

Kerr, Daniel J. ^{[1
]}

Flynn, Bernard L. ^{[1
]}

机构：

[1] Monash Univ, Monash Inst Pharmaceut Sci, Parkville, Vic 3052, Australia

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 07期

基金：

澳大利亚研究理事会;

关键词：

NAZAROV CYCLIZATION; ASYMMETRIC-SYNTHESIS; TRICYCLIC CORE; BRONSTED ACID; ROSEOPHILIN; CYCLOPENTENONES;

D O I：

10.1021/ol300332b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convergent reaction sequence involving a reductive coupling and a chiral Bronsted acid catalyzed Nazarov reaction is utilized in a concise formal synthesis of (+)-roseophilin (11 steps via longest linear sequence, 10.2% yield, 95% ee).

引用

页码：1740 / 1743

页数：4

共 42 条

[1] Enantioselective formal total synthesis of roseophilin [J].

Bamford, SJ ;

Luker, T ;

Speckamp, WN ;

Hiemstra, H .

ORGANIC LETTERS, 2000, 2 (08) :1157-1160

[2] α-Hydroxy cyclopentenones from α-diketones [J].

Batson, WA ;

Sethumadhavan, D ;

Tius, MA .

ORGANIC LETTERS, 2005, 7 (13) :2771-2774

[3] The palladium(II)-catalyzed Nazarov reaction [J].

Bee, C ;

Leclerc, E ;

Tius, MA .

ORGANIC LETTERS, 2003, 5 (26) :4927-4930

[4] Formal Synthesis of (±)-Roseophilin [J].

Bitar, Abdallah Y. ;

Frontier, Alison J. .

ORGANIC LETTERS, 2009, 11 (01) :49-52

[5] Asymmetric total synthesis of ent-(-)-roseophilin:: Assignment of absolute configuration [J].

Boger, DL ;

Hong, JY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (35) :8515-8519

[6]

Cao P., 2010, ANGEW CHEM, V122, P4565

[7] Asymmetric Nazarov Reaction Catalyzed by Chiral Tris(oxazoline)/Copper(II) [J].

Cao, Peng ;

Deng, Chao ;

Zhou, You-Yun ;

Sun, Xiu-Li ;

Zheng, Jun-Cheng ;

Xie, Zuowei ;

Tang, Yong .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (26) :4463-4466

[8] The Nazarov cyclization in organic synthesis. Recent advances [J].

Frontier, AJ ;

Collison, C .

TETRAHEDRON, 2005, 61 (32) :7577-7606

[9] The core structures of roseophilin and the prodigiosin alkaloids define a new class of protein tyrosine phosphatase inhibitors [J].

Fürstner, A ;

Reinecke, K ;

Prinz, H ;

Waldmann, H .

CHEMBIOCHEM, 2004, 5 (11) :1575-1579

[10]

Fürstner A, 2001, CHEMBIOCHEM, V2, P706, DOI 10.1002/1439-7633(20010903)2:9<706::AID-CBIC706>3.0.CO

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