STUDIES ON THE SYNTHESES OF BIOLOGICALLY-ACTIVE SESQUITERPENE LACTONES

被引:15
作者
ANDO, M
机构
关键词
EUDESMANOLIDES; ELEMANOLIDES; GUAIANOLIDES; FRAGMENTATION REACTION; SOLVOLYTIC REARRANGEMENT; BIOLOGICALLY ACTIVE SESQUITERPENE LACTONES;
D O I
10.5059/yukigoseikyokaishi.50.858
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Many biologically interesting eudesmanolides have been synthesized from commercilly available alpha-santonin and their biological activities have been studies. The eudesmanolides functionalized at C-1 were then demonstrated to be efficient common intermediates for the syntheses of elemanolides and guaianolides. Thus the fragmentation reaction of 36 with Al (i PrO)3 gave a new route to the synthesis of elemanolides and germacranolides. The solvolytic rearrangement of 36, 49, 63, and 99 gave efficient intermediates for the syntheses of naturally occurring guaianolides.
引用
收藏
页码:858 / 874
页数:17
相关论文
共 39 条
[1]   STUDIES ON SYNTHESES OF SESQUITERPENE LACTONES .5. TOTAL SYNTHESIS OF ARBORESCIN [J].
ANDO, M ;
AKAHANE, A ;
TAKASE, K .
CHEMISTRY LETTERS, 1978, (07) :727-730
[2]   STUDIES ON THE SYNTHESES OF SESQUITERPENE LACTONES .3. IMPROVED SYNTHESIS OF VULGARIN [J].
ANDO, M ;
TAJIMA, K ;
TAKASE, K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (09) :2737-2738
[3]   STUDIES ON SYNTHESES OF SESQUITERPENE LACTONES .4. TOTAL SYNTHESIS OF SAUSSUREA LACTONE [J].
ANDO, M ;
TAJIMA, K ;
TAKASE, K .
CHEMISTRY LETTERS, 1978, (06) :617-620
[4]   STUDIES ON SYNTHESES OF SESQUITERPENE LACTONES .1. CHEMICAL TRANSFORMATION OF ALPHA-SANTONIN INTO VULGARIN, C4-EPIVULGARIN, AND ARGLANINE [J].
ANDO, M ;
AKAHANE, A ;
TAKASE, K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1978, 51 (01) :283-289
[5]   STUDIES ON THE SYNTHESES OF SESQUITERPENE LACTONES .6. TOTAL SYNTHESES OF ZALUZANIN-C, ZALUZANIN-D, AND 3-EPIZALUZANIN-C [J].
ANDO, M ;
YAMAOKA, H ;
TAKASE, K .
CHEMISTRY LETTERS, 1982, (04) :501-504
[6]   STUDIES ON THE SYNTHESES OF SESQUITERPENE LACTONES .9. TOTAL SYNTHESES OF MOKKO LACTONE, DEHYDROCOSTUS LACTONE, AND EREMANTHIN [J].
ANDO, M ;
ONO, A ;
TAKASE, K .
CHEMISTRY LETTERS, 1984, (04) :493-496
[7]   SYNTHESES OF ARBORESCIN, 1,10-EPIARBORESCIN, AND (11S)-GUAIA-3,10(14)-DIENO-13,6-ALPHA-LACTONE, THE KEY INTERMEDIATE IN GREENE AND CRABBES ESTAFIATIN SYNTHESIS, AND THE STEREOCHEMICAL ASSIGNMENT OF ARBORESCIN [J].
ANDO, M ;
AKAHANE, A ;
YAMAOKA, H ;
TAKASE, K .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (20) :3909-3916
[8]   STUDIES ON THE SYNTHESES OF SESQUITERPENE LACTONES .10. IMPROVED SYNTHESES OF (+)-TUBERIFERIN AND THE RELATED ALPHA-METHYLENE GAMMA-LACTONES AND THEIR BIOLOGICAL-ACTIVITIES [J].
ANDO, M ;
WADA, T ;
KUSAKA, H ;
TAKASE, K ;
HIRATA, N ;
YANAGI, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (21) :4792-4796
[9]   STUDIES ON THE SYNTHESES OF SESQUITERPENE LACTONES .13. SYNTHESIS OF FUNCTIONALIZED ENDOCYCLIC ALPHA,BETA-UNSATURATED AND ALPHA-METHYLENE EUDESMANOLIDES [J].
ANDO, M ;
WADA, T ;
ISOGAI, K .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (21) :6235-6238
[10]   STUDIES ON THE SYNTHESIS OF SESQUITERPENE LACTONES .12. SYNTHESIS OF (+)-COLARTIN, (+)-ARBUSCULIN-A, AND THEIR C-4 EPIMERS AND THEIR BIOLOGICAL-ACTIVITIES [J].
ANDO, M ;
ISOGAI, K ;
AZAMI, H ;
HIRATA, N ;
YANAGI, Y .
JOURNAL OF NATURAL PRODUCTS, 1991, 54 (04) :1017-1024