INTRAMOLECULAR DIELS-ALDER REACTIONS OF VINYLFURANS LEADING TO FURANODECALINS

被引：11

作者：

CORNWALL, P ^{[1
]}

DELL, CP ^{[1
]}

KNIGHT, DW ^{[1
]}

机构：

[1] CHEM DEPT,UNIV PK,NOTTINGHAM NG7 2RD,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 20期

关键词：

D O I：

10.1039/p19930002395

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Thermolysis of the (2E,8Z)-9-(2-furyl)nonadienoate 25 at 290-degrees-C leads to an essentially quantitative yield of a single furanodecalin 26, whereas the corresponding (2E,8E)-isomer 34 undergoes a non-stereoselective cyclisation leading to the furanodecalins 26 and 35. (Z)-Alkenoate functions undergo partial isomerisation prior to cyclisation and so lead to mixtures of isomers. Alkyl groups can be incorporated around the reaction sites, but this can result in overwhelming competition from side reactions. The corresponding 3-furyl analogues 56 and 59 display very similar reactivities.

引用

页码：2395 / 2405

页数：11

共 86 条

[81] STEREOCONTROLLED APPROACH TO STEROID SIDE-CHAIN VIA ORGANOPALLADIUM CHEMISTRY - PARTIAL SYNTHESIS OF 5-ALPHA-CHOLESTANONE [J].