Total synthesis of (±)-rocaglamide and some aryl analogues

被引：56

作者：

Dobler, MR

Bruce, I

Cederbaum, F

Cooke, NG

Diorazio, LJ

Hall, RG

Irving, E

机构：

[1] Novartis Crop Protect AG, CH-4002 Basel, Switzerland

[2] Novartis Pharmaceut, Cent Res, Macclesfield SK10 2NX, Cheshire, England

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 47期

关键词：

D O I：

10.1016/S0040-4039(01)01807-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The insecticidal activity found for rocaglamide and its congeners, prompted us to establish a short and efficient synthesis of the natural product and some synthetic 'halo-aryl' analogues. Pd-catalysed cross-coupling reactions of the bromo analogue were then explored in order to gain a suitable access to a broad range of unnatural analogues. The key step of our approach is a keto-aldehyde acyloin ring-closure followed by a Stiles carboxylation. (C) 2001 Elsevier Science Ltd. All rights reserved.

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页码：8281 / 8284

页数：4

相关论文

共 19 条

[1] SYNTHESIS OF THE NOVEL ANTILEUKEMIC TETRAHYDROCYCLOPENTA[B]BENZOFURAN, ROCAGLAMIDE [J].

DAVEY, AE ;

SCHAEFFER, MJ ;

TAYLOR, RJK .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (16) :1137-1139

[2] A NOVEL 1,3-DITHIANE-BASED CYCLOPENTA-ANNELLATION PROCEDURE - SYNTHESIS OF THE ROCAGLAMIDE SKELETON [J].

DAVEY, AE ;

TAYLOR, RJK .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (01) :25-27

[3]

DAVEY AE, 1992, J CHEM SOC P1, V112, P2657

[4] CHELATION AS A DRIVING FORCE IN ORGANIC REACTIONS .4 SYNTHESIS OF ALPHA-NITRO ACIDS BY CONTROL OF CARBOXYLATION-DECARBOXYLATION EQUILIBRIUM [J].

FINKBEINER, HL ;

STILES, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (05) :616-&

[5]

Gussregen B, 1997, Z NATURFORSCH C, V52, P339

[6] New insecticidal rocaglamide derivatives from the roots of Aglaia duperreana [J].

Hiort, J ;

Chaidir ;

Bohnenstengel, FI ;

Nugroho, BW ;

Schneider, C ;

Wray, V ;

Witte, L ;

Hung, PD ;

Kiet, LC ;

Proksch, P .

JOURNAL OF NATURAL PRODUCTS, 1999, 62 (12) :1632-1635

[7] A SYNTHETIC APPROACH TO ROCAGLAMIDE VIA REDUCTIVE CYCLIZATION OF DELTA-KETO NITRILES [J].

KRAUS, GA ;

SY, JO .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (01) :77-83

[8]

Littke AF, 1998, ANGEW CHEM INT EDIT, V37, P3387, DOI 10.1002/(SICI)1521-3773(19981231)37:24<3387::AID-ANIE3387>3.0.CO

[9]

2-P

[10] Insecticidal rocaglamide derivatives from Aglaia duppereana [J].

Nugroho, BW ;

Edrada, RA ;

Gussregen, B ;

Wray, V ;

Witte, L ;

Proksch, P .

PHYTOCHEMISTRY, 1997, 44 (08) :1455-1461