STUDIES ON THE SYNTHESIS OF SESQUITERPENE LACTONES .14. SYNTHESES OF (-)-ARBUSCLIN-D AND (+)-4-EPI-ARBUSCLIN-D - THE STEREOCHEMICAL ASSIGNMENT OF ARBUSCLIN-D

被引:14
作者
ANDO, M
ISOGAI, K
AZAMI, H
HIRATA, N
YAMAZAKI, H
YANAGI, Y
机构
[1] TOHOKU UNIV,FAC SCI,DEPT CHEM,AOBA KU,SENDAI,MIYAGI 980,JAPAN
[2] SUMITOMO CHEM CO LTD,AGR SCI RES LAB,TAKARAZUKA,HYOGO 665,JAPAN
[3] SUMITOMO PHARMACEUT CO LTD,DIV CLIN RES & DEV,CHIYODA KU,TOKYO 101,JAPAN
来源
JOURNAL OF NATURAL PRODUCTS | 1992年 / 55卷 / 11期
关键词
D O I
10.1021/np50089a009
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Efficient syntheses of (-)-arbusclin D and (+)-4-epi-arbusclin D are reported. By these syntheses the C-4 stereochemistry of arbusclin D and the absolute configuration of (-)-arbusclin D have been determined to be a s shown in structure 1. The biological activities, such as cytotoxic activity toward P-388 lymphocytic leukemia, plant growth regulating activity, and antimicrobial activity of compounds 1, 3, 7, 9, 12, and 14 were also studied.
引用
收藏
页码:1620 / 1625
页数:6
相关论文
共 6 条
[1]   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
[2]   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
[3]   SESQUITERPENE LACTONES OF ARTEMISIA SPECIES . NEW LACTONES FROM A-ARBUSCULA SSP ARBUSCULA AND A-TRIPARTITA SSP RUPICOLA [J].
IRWIN, MA ;
GEISSMAN, TA .
PHYTOCHEMISTRY, 1969, 8 (12) :2411-&
[4]   ARBUSCULIN-D FROM ARTEMISIA-ARBUSCULA SSP-ARBUSCULA [J].
IRWIN, MA ;
GEISSMAN, TA .
PHYTOCHEMISTRY, 1973, 12 (04) :853-855
[5]  
MASSANET GM, 1991, J ORG CHEM, V56, P3587
[6]   STUDIES ON TERPENOIDS AND RELATED ALICYCLIC COMPOUNDS .11. CHEMICAL TRANSFORMATION OF ALPHA-SANTONIN INTO BALCHANIN, COLARTIN, AND ARBUSCULIN-A, ARBUSCULIN-B, ARBUSCULIN-C AND ARBUSCULIN-E [J].
YAMAKAWA, K ;
NISHITANI, K ;
AZUSAWA, K .
HETEROCYCLES, 1977, 8 :103-108