The chemistry and occurrence of taxane derivatives .24. Acid and base catalysed rearrangements of 9,10-dioxotaxanes

被引：14
作者：
Appendino, G
Jakupovic, J
Varese, M
Bombardelli, E
机构：
[1] TECH UNIV BERLIN,INST ORGAN CHEM,D-10623 BERLIN,GERMANY
[2] INDENA SPA,I-20141 MILAN,ITALY
来源：
TETRAHEDRON LETTERS | 1996年 / 37卷 / 05期
关键词：
D O I：
10.1016/0040-4039(95)02254-6
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Treatment of 10-dehydro-10-deacetylbaccatin III (2a) with trichloroacetic acid gave the bis-abeotaxane 3, whereas treatment of 2a and its 7-epimer (2b) with bases (DBU, NaH) triggered a tandem retroaldol-Michael reaction, giving a compound of the 7,8-seco-8,12-cyclotaxane type. Both skeletal rearrangements were accompanied by extensive reorganisation of the oxygen functions in the southern hemisphere of the molecule.
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页码：727 / 730
页数：4
相关论文
共 11 条
[1]   THE PHYTOCHEMISTRY OF THE YEW TREE [J].
APPENDINO, G .
NATURAL PRODUCT REPORTS, 1995, 12 (04) :349-360
[2]  
APPENDINO G, 1994, TETRAHEDRON LETT, P2217
[3]  
APPENDINO G, 1994, GAZZ CHIM ITAL, V24, P253
[4]  
APPENDINO G, 1995, CHEM PHARM TAXOL ITS, P13
[5]   GEOMETRICAL REACTION COORDINATES .2. NUCLEOPHILIC ADDITION TO A CARBONYL GROUP [J].
BURGI, HB ;
DUNITZ, JD ;
SHEFTER, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (15) :5065-5067
[6]   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
[7]   TAXINE .6. STEREOCHEMISTRY OF TAXICIN-1 AND TAXICIN-2 [J].
EYRE, DH ;
HARRISON, JW ;
LYTHGOE, B .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (06) :452-&
[8]  
GABETTA B, 1995, IN PRESS PHYTOCHEMIS
[9]   ANTI-LEUKEMIC ALKALOIDS FROM TAXUS-WALLICHIANA ZUCC [J].
MILLER, RW ;
POWELL, RG ;
SMITH, CR ;
ARNOLD, E ;
CLARDY, J .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (07) :1469-1474
[10]  
TORREGIANI E, 1995, TETRAHEDRON LETT, P7127
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