A SHORTER ROUTE TO THE SYNTHESIS OF (+)-JUNENOL, ISOJUNENOL, AND THEIR COUMARATE ESTERS FROM (-)-SANTONIN

被引:25
作者
CARDONA, L [1 ]
GARCIA, B [1 ]
GIMENEZ, JE [1 ]
PEDRO, JR [1 ]
机构
[1] VALENCIA UNIV,FAC CHEM,DEPT ORGAN CHEM,E-46100 BURJASSOT,SPAIN
关键词
D O I
10.1016/S0040-4020(01)88189-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This paper reports on the chemical conversion of (-)-santonin into (+)-junenol, isojunenol and their coumarate esters. The identity of (1)-junenol and 8-epi-beta-verbesinol is also established.
引用
收藏
页码:851 / 860
页数:10
相关论文
共 24 条
[1]   SYNTHETIC STUDIES ON TERPENOIDS .7. SYNTHETIC STUDIES LEADING TO THE TOTAL SYNTHESIS OF EUDESMANE SESQUITERPENES [J].
BANERJEE, AK ;
HURTADO, HE ;
DECARRASCO, MC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (11) :2547-2551
[2]  
BHATTACHARYYA SC, 1962, TETRAHEDRON, V18, P969
[3]   SYNTHESIS OF VARIOUS NATURAL 8,12-ELEMANOLIDES FROM ARTEMISIN [J].
BLAY, G ;
FERNANDEZ, I ;
GARCIA, B ;
PEDRO, JR .
TETRAHEDRON, 1989, 45 (18) :5925-5934
[4]   FUNCTIONALITY TRANSFER FROM C-6 TO C-8 IN SESQUITERPENES - SYNTHESIS OF 8-EPI-IVANGUSTIN AND 8-EPI-ISOIVANGUSTIN FROM SANTONIN [J].
BLAY, G ;
CARDONA, ML ;
GARCIA, B ;
PEDRO, JR .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (21) :6172-6175
[5]  
BOHLMANN F, 1982, PHYTOCHEMISTRY, V21, P2899
[6]   NATURAL TERPENE DERIVATIVES .224. CONFIGURATION OF ALPHA-VERBESINOL COUMARATE AND BETA-VERBESINOL COUMARATE [J].
BOHLMANN, F ;
ZDERO, C .
PHYTOCHEMISTRY, 1979, 18 (10) :1751-1752
[7]   NATURALLY-OCCURRING TERPENE DERIVATIVES .431. GERMACRANE AND EUDESMANE DERIVATIVES FROM CALEA-RETICULATA [J].
BOHLMANN, F ;
BORTHAKUR, N ;
KING, RM ;
ROBINSON, H .
PHYTOCHEMISTRY, 1982, 21 (07) :1793-1794
[8]   NATURALLY OCCURRING TERPENE DERIVATIVES .232. NEW LABDANE DERIVATIVE AND SESQUITERPENE IN SILPHIUM SPECIES [J].
BOHLMANN, F ;
JAKUPOVIC, J .
PHYTOCHEMISTRY, 1979, 18 (12) :1987-1992
[9]  
BOHLMANN F, 1983, PHYTOCHEMISTRY, V20, P983
[10]   THE CHEMISTRY OF SANTONIN .3. THE STEREOCHEMISTRY OF SOME REDUCTION PRODUCTS OF SANTONIN [J].
COCKER, W ;
MCMURRY, TBH .
JOURNAL OF THE CHEMICAL SOCIETY, 1956, (NOV) :4549-4557