Regio- and stereoselective oxyfunctionalization at C-1 and C-5 in sesquiterpene guaianolides

被引:27
作者
Bargues, V [1 ]
Blay, G [1 ]
Cardona, L [1 ]
García, B [1 ]
Pedro, JR [1 ]
机构
[1] Univ Valencia, Fac Quim, Dept Quim Organ, E-46100 Valencia, Spain
关键词
D O I
10.1016/S0040-4020(97)10392-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The regio- and stereoselective functionalization at C-1 and C-5 positions in a guaiane skeleton by allylic hydroxylation are described The stereochemistry of the resulting compounds are identical to those of the majority of natural 1- and 5-hydroxy-guaianolides. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1845 / 1852
页数:8
相关论文
共 31 条
[1]   STUDIES ON THE SYNTHESIS OF SESQUITERPENE LACTONES .16. THE SYNTHESES OF 11-BETA,13-DIHYDROKAUNIOLIDE, ESTAFIATIN, ISODEHYDROCOSTUSLACTONE, 2-OXODESOXYLIGUSTRIN, ARBORESCIN, 1,10-EPIARBORESCIN, 11-BETA,13-DIHYDROLUDARTIN, 8-DEOXY-11-BETA,13-DIHYDRORUPICOLIN-B, 8-DEOXYRUPICOLIN-B, 3,4-EPILUDARTIN, LUDARTIN, KAUNIOLIDE, DEHYDROLEUCODIN, AND LEUCODIN [J].
ANDO, M ;
IBAYASHI, K ;
MINAMI, N ;
YOSHIMURA, H ;
NAKAMURA, T ;
ISOGAI, K .
JOURNAL OF NATURAL PRODUCTS, 1994, 57 (04) :433-445
[2]   FULVENE LACTONES FROM TANACETUM-ANNUUM [J].
BARRERO, AF ;
SANCHEZ, JF ;
ZAFRA, MJ ;
BARRON, A ;
FELICIANO, AS .
PHYTOCHEMISTRY, 1987, 26 (05) :1531-1533
[3]   GUAIANOLIDES FROM TANACETUM-ANNUUM [J].
BARRERO, AF ;
SANCHEZ, JF ;
MOLINA, J ;
BARRON, A ;
SALAS, MD .
PHYTOCHEMISTRY, 1990, 29 (11) :3575-3580
[4]   PHOTOCHEMICAL TRANSFORMATIONS .1. SOME PRELIMINARY INVESTIGATIONS [J].
BARTON, DHR ;
DEMAYO, P ;
SHAFIQ, M .
JOURNAL OF THE CHEMICAL SOCIETY, 1957, (MAR) :929-935
[5]   BISMETHYLENEDIOXY STEROIDS .3. THE SYNTHESIS OF 7-ALPHA-METHYLHYDROCORTISONES AND 7-BETA-METHYLHYDROCORTISONES [J].
BEYLER, RE ;
OBERSTER, AE ;
HOFFMAN, F ;
SARETT, LH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (01) :170-178
[6]   Ring-opening aminolysis of sesquiterpene lactones: An easy entry to bioactive sesquiterpene derivatives. Synthesis of (+)-beta-cyperone and (-)-eudesma-3,5-diene from santonin. [J].
Blay, G ;
Cardona, L ;
Garcia, B ;
Garcia, CL ;
Pedro, JR .
TETRAHEDRON, 1996, 52 (31) :10507-10518
[7]   Stereoselective synthesis of 8,12-furanoeudesmanes from santonin. Absolute stereochemistry of natural furanoeudesma-1,3-diene and tubipofurane [J].
Blay, G ;
Cardona, L ;
Garcia, B ;
Pedro, JR ;
Sanchez, JJ .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3815-3819
[8]   GUAIANOLIDES RELATED TO ARBORESCIN FROM ARTEMISIA-ADAMSII [J].
BOHLMANN, F ;
HARTONO, L ;
JAKUPOVIC, J ;
HUNECK, S .
PHYTOCHEMISTRY, 1985, 24 (05) :1003-1007
[9]   NATURALLY-OCCURRING TERPENE DERIVATIVES .358. 4 GUAIANOLIDES AND OTHER CONSTITUENTS FROM 3 KAUNIA SPECIES [J].
BOHLMANN, F ;
KRAMP, W ;
GUPTA, RK ;
KING, RM ;
ROBINSON, H .
PHYTOCHEMISTRY, 1981, 20 (10) :2375-2378
[10]  
CAMPS F, 1978, SYNTHESIS-STUTTGART, P215