SYNTHESIS OF (+/-)-KARAHANA ETHER AND KARAHANAENONE BY SELECTIVE CYCLIZATION OF 6,7-EPOXYGERANYL ACETATE

被引:33
作者
BARRERO, AF
ALVAREZMANZANEDA, EJ
PALOMINO, PL
机构
[1] Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Granada
关键词
D O I
10.1016/S0040-4020(01)89332-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Efficient methods for preparing (+/-)-karahana ether (1b) and karahanaenone (2) from 6,7-epoxygeranyl acetate(3), by Lewis-acid-catalyzed electrophilic cyclization, are described.
引用
收藏
页码:13239 / 13250
页数:12
相关论文
共 23 条
[1]   SYNTHESIS OF (+/-)-KARAHANA ETHER AND A (+/-)-LABDADIENOIC ACID BY THE ELECTROPHILIC CYCLIZATION OF EPOXY ALLYLSILANES [J].
ARMSTRONG, RJ ;
WEILER, L .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1986, 64 (03) :584-596
[2]   SYNTHESIS OF (+/-)-TRIXAGOL BY AN ELECTROPHILIC CYCLIZATION OF AN ALLYLSILANE [J].
ARMSTRONG, RJ ;
WEILER, L .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1983, 61 (11) :2530-2539
[3]   SYNTHESIS OF RACEMIC AND OPTICALLY-ACTIVE FORMS OF A FAMILY OF NATURALLY OXYGENATED UMBELLIFERONE DERIVATIVES - 3-DIMENSIONAL STRUCTURE OF (-)3',6'-EPOXYAURAPTEN [J].
AZIZ, M ;
ROUESSAC, F .
TETRAHEDRON, 1988, 44 (01) :101-110
[4]  
AZIZ M, 1988, B SOC CHIM FR, P55
[5]   SYNTHESIS OF AMBROX(R) FROM (-)-SCLAREOL AND (+)-CIS-ABIENOL [J].
BARRERO, AF ;
ALVAREZMANZANEDA, EJ ;
ALTAREJOS, J ;
SALIDO, S ;
RAMOS, JM .
TETRAHEDRON, 1993, 49 (45) :10405-10412
[6]   SYNTHESIS OF AMBROX(R) FROM COMMUNIC ACIDS [J].
BARRERO, AF ;
ALTAREJOS, J ;
ALVAREZMANZANEDA, EJ ;
RAMOS, JM ;
SALIDO, S .
TETRAHEDRON, 1993, 49 (28) :6251-6262
[7]  
BARRERO AF, 1993, TETRAHEDRON, V42, P9525
[8]  
CAIRNS MP, 1982, TETRAHEDRON LETT, V23, P1405
[9]   TOTAL SYNTHESIS OF +/- KARAHANA ETHER [J].
COATES, RM ;
MELVIN, LS .
JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (03) :865-&