BICYCLOANNULATION OF ALPHA-BROMO ALPHA,BETA-UNSATURATED ESTERS - SYNTHESIS OF THE TRICYCLO[4.4.0.0(1,5)]DECANE FRAMEWORK AND ITS CONGENERS

被引:17
作者
HAGIWARA, H
ABE, F
UDA, H
机构
[1] Institute for Chemical Reaction Science, Tohoku University, Katahira, Aoba-ku
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 21期
关键词
D O I
10.1039/p19930002651
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reactions of the kinetic enolates 6 of 1-acetylcyclohexenes 5 with alpha-bromo alpha,beta-unsaturated esters proceed via a successive Michael-Michael-substitution pathway to give methyl 2-oxotricyclo-[4.4.0.0(1,5)]decane-5-carboxylates 8 in a one-pot operation.
引用
收藏
页码:2651 / 2655
页数:5
相关论文
共 25 条
[1]   NATURALLY-OCCURRING TERPENE DERIVATIVES .369. LABDANE DERIVATIVES FROM HEMIZONIA SPECIES [J].
BOHLMANN, F ;
JAKUPOVIC, J ;
AHMED, M ;
WALLMEYER, M ;
ROBINSON, H ;
KING, RM .
PHYTOCHEMISTRY, 1981, 20 (10) :2383-2387
[2]   NATURALLY-OCCURRING TERPENE DERIVATIVES .423. 11-HYDROXY-ALPHA-CUBEBENE AND BETA-CUBEBENE FROM EUPATORIUM-SEROTINUM [J].
BOHLMANN, F ;
JAKUPOVIC, J ;
VOGEL, W .
PHYTOCHEMISTRY, 1982, 21 (05) :1153-1154
[3]  
COLL JC, 1986, B SOC CHIM BELG, V95, P815
[4]  
Connolly J. D. H., 1991, DICT TERPENOIDS
[5]   DIELS-ALDER REACTIONS OF TRANS-1-METHOXY-3-TRIMETHYLSILYLOXY-1,3-BUTADIENE [J].
DANISHEFSKY, S ;
KITAHARA, T ;
YAN, CF ;
MORRIS, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (23) :6996-7000
[6]   CYCLIZATION OF METHYL ALPHA-BROMOCROTONATE TO A PENTASUBSTITUTED CYCLOPROPANE [J].
DUHAMEL, L ;
PESCHARD, O ;
PLE, G .
TETRAHEDRON LETTERS, 1991, 32 (36) :4695-4698
[7]   BICYCLOANNULATION LEADING TO THE TRICYCLO[4.4.0.0(1,5)]DECANE FRAMEWORK AND ITS CONGENERS [J].
HAGIWARA, H ;
ABE, F ;
UDA, H .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (16) :1070-1071
[8]   TOTAL SYNTHESIS OF (+)-DIHYDROCOMPACTIN [J].
HAGIWARA, H ;
KONNO, M ;
UDA, H .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (12) :866-868
[10]   SESQUITERPENE THIOCYANATES AND ISOTHIOCYANATES FROM AXINYSSA-APLYSINOIDES [J].
HE, HY ;
SALVA, J ;
CATALOS, RF ;
FAULKNER, DJ .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (11) :3191-3194