Further unexpected boron trifluoride-catalyzed reactions of taxoids with α- and β-4,20-epoxides

被引:9
作者
Hosoyama, H [1 ]
Shigemori, H [1 ]
Kobayashi, J [1 ]
机构
[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Kita Ku, Sapporo, Hokkaido 0600812, Japan
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 03期
关键词
D O I
10.1039/a905799d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Three unusual taxinine derivatives, the cyclobutane 3, the dioxane 4, and the orthoester 5, were obtained by boron trifluoride-catalyzed reactions of beta- and alpha-4,20-epoxy-5-O-triethylsilyltaxinine A (1 and 2, respectively) (3 and 4 from 1; 5 from 2).
引用
收藏
页码:449 / 451
页数:3
相关论文
共 7 条
[1]   THE PHYTOCHEMISTRY OF THE YEW TREE [J].
APPENDINO, G .
NATURAL PRODUCT REPORTS, 1995, 12 (04) :349-360
[2]   THE CHEMISTRY OF TAXANES - REACTION OF TAXOL AND BACCATIN DERIVATIVES WITH LEWIS-ACIDS IN APROTIC AND PROTIC MEDIA [J].
CHEN, SH ;
HUANG, S ;
WEI, JM ;
FARINA, V .
TETRAHEDRON, 1993, 49 (14) :2805-2828
[3]   Stereoselective epoxidation of 4(20)-exomethylene in taxinine derivatives and assignment of the epoxide orientation by NMR [J].
Hosoyama, H ;
Shigemori, H ;
In, Y ;
Ishida, T ;
Kobayashi, J .
TETRAHEDRON, 1998, 54 (11) :2521-2528
[4]   Unusual boron trifluoride-catalyzed reactions of taxinine derivatives with α- and β-4(20)-epoxides [J].
Hosoyama, H ;
Shigemori, H ;
Kobayashi, J .
TETRAHEDRON LETTERS, 1999, 40 (11) :2149-2152
[5]   Occurrence of a new dimeric compound of 5-oxotaxinine A through Diels-Alder cycloaddition [J].
Hosoyama, H ;
Shigemori, H ;
In, Y ;
Ishida, T ;
Kobayashi, J .
TETRAHEDRON LETTERS, 1998, 39 (15) :2159-2162
[6]  
KINGSTON DGI, 1993, PROG CHEM ORG NAT PR, V61, P1
[7]   TAXUSPINES-A-C, NEW TAXOIDS FROM JAPANESE YEW TAXUS-CUSPIDATA INHIBITING DRUG TRANSPORT ACTIVITY OF P-GLYCOPROTEIN IN MULTIDRUG-RESISTANT CELLS [J].
KOBAYASHI, J ;
OGIWARA, A ;
HOSOYAMA, H ;
SHIGEMORI, H ;
YOSHIDA, N ;
SASAKI, T ;
LI, Y ;
IWASAKI, S ;
NAITO, M ;
TSURUO, T .
TETRAHEDRON, 1994, 50 (25) :7401-7416