Intramolecular organocatalytic [3+2] dipolar cycloaddition:: Stereospecific cycloaddition and the total synthesis of (±)-hirsutene

被引：174

作者：

Wang, JC ^{[1
]}

Krische, MJ ^{[1
]}

机构：

[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 47期

关键词：

cycloaddition; natural products; organocatalysis; phosphanes;

D O I：

10.1002/anie.200352218

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A testing ground for cyclopentannulation strategies: the triquinane natural product hirsutene is obtained through the intramolecular organocatalytic [3+2] cycloaddition of the 1,7-enyne (E)-1. The cycloaddition is stereospecific: reaction of the corresponding Z isomer provides the epimeric diquinane.

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页码：5855 / 5857

页数：3

相关论文

共 27 条

[1] Catalytic crossed Michael cycloisomerization of thioenoates:: Total synthesis of (±)-ricciocarpin A [J].

Agapiou, K ;

Krische, MJ .

ORGANIC LETTERS, 2003, 5 (10) :1737-1740

[2] Recent advances in the Baylis-Hillman reaction and applications [J].

Basavaiah, D ;

Rao, AJ ;

Satyanarayana, T .

CHEMICAL REVIEWS, 2003, 103 (03) :811-891

[3] PREPARATION OF LITHIUM ACETYLIDE.ETHYLENEDIAMINE [J].

BEUMEL, OF ;

HARRIS, RF .

JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (10) :2775-&

[4] CHLORIOLINS A-C, CHLORINATED SESQUITERPENES PRODUCED BY FUNGAL CULTURES SEPARATED FROM A JASPIS MARINE SPONGE [J].

CHENG, XC ;

VAROGLU, M ;

ABRELL, L ;

CREWS, P ;

LOBKOVSKY, E ;

CLARDY, J .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) :6344-6348

[5] STRUCTURE OF HIRSUTIC ACID . X-RAY ANALYSIS OF P-BROMOPHENACYL ESTER [J].

COMER, FW ;

TROTTER, J .

JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1966, (01) :11-&

[6]

Dalko P. I., 2001, ANGEW CHEM-GER EDIT, V113, P3840

[7]

Dalko PI, 2001, ANGEW CHEM INT EDIT, V40, P3726, DOI 10.1002/1521-3773(20011015)40:20<3726::AID-ANIE3726>3.0.CO

[8]

2-D

[9] Highly regioselective construction of spirocycles via phosphine-catalyzed [3+2]-cycloaddition [J].

Du, YS ;

Lu, XY ;

Yu, YH .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (25) :8901-8905

[10] REINVESTIGATION ON THE CATALYTIC ISOMERIZATION OF CARBON-CARBON TRIPLE BONDS [J].

GUO, C ;

LU, XY .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (16) :1921-1923