Synthesis of spiro [5.4] decenones and their transformation into bicyclo[4.4]deca-1,4-dien-3-ones by domino "elimination-double-Wagner-Meerwein-rearrangement" reactions

被引：9

作者：

Bose, G ^{[1
]}

Ullah, E ^{[1
]}

Langer, P ^{[1
]}

机构：

[1] Univ Greifswald, Inst Chem & Biochem, D-17487 Greifswald, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2004年 / 10卷 / 23期

关键词：

cyclization; domino reactions; rearrangments; silyl enol ethers; spiro compounds;

D O I：

10.1002/chem.200400707

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The [3+3] cyclization of 1,3-bis-silyl enol ethers with 1,1-diacylcyclopentanes allows a convenient synthesis of spiro[5.4]decenones. Treatment of these compounds with trifluoroacetic acid (TFA) afforded a great variety of bicyclo [4.4.0]deca-1,4-dien-3-ones containing an angular alkyl group. This core structure occurs in a number of pharmacologically relevant natural products.

引用

页码：6015 / 6028

页数：14

共 55 条

[1]

ADAM W, 1995, SYNTHESIS-STUTTGART, P1163

[2]

[Anonymous], 1997, ROMPP LEXIKON NATURS

[3] NEIGHBORING CARBON AND HYDROGEN .46. SPIRO-(4,5)-DECA-1,4-DIENE-3-ONE FROM AR1THETA-5 PARTICIPATION [J].

BAIRD, R ;

WINSTEIN, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (05) :788-&

[4] CONVENIENT SYNTHESES OF 5-SUBSTITUTED 2-HYDROXYBENZOATES AND RELATED REACTIONS [J].

BARTON, DHR ;

DRESSAIRE, G ;

WILLIS, BJ ;

BARRETT, AGM ;

PFEFFER, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (03) :665-669

[5]

Bednarski M.D., 1991, COMPREHENSIVE ORGANI, V2, P661, DOI DOI 10.1016/B978-0-08-052349-1.00044-5

[6] THE AROMATIZATION AND REARRANGEMENT OF CYCLIC KETONES .2. 3-PHENYL-5,5-DIMETHYLCYCLOHEXENONE [J].

BERINGER, M ;

KUNTZ, I .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (01) :364-366

[7] SYNTHESIS OF BICYCLO[3.3.1]NONANE DERIVATIVES UNDER PHYSIOLOGICAL CONDITIONS [J].

BERTZ, SH ;

DABBAGH, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1982, 21 (04) :306-307

[8]

BERTZ SH, 1982, ANGEW CHEM, V94, P317

[9] CHEMISTRY OF ENOL SILYL ETHERS - A GENERAL-SYNTHESIS OF 3-HYDROXYHOMOPHTHALATES AND A BIOMIMETIC SYNTHESIS OF SCLERIN .12. [J].

BROWNBRIDGE, P ;

CHAN, TH ;

BROOK, MA ;

KANG, GJ .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1983, 61 (04) :688-693

[10]

BUCHI G, 1980, J ORG CHEM, V27, P827

← 1 2 3 4 5 6 →