REGIOSELECTIVE DEMETHYLATION OF ACONITINE

被引:17
作者
BLAGBROUGH, IS [1 ]
HARDICK, DJ [1 ]
WONNACOTT, S [1 ]
POTTER, BVL [1 ]
机构
[1] UNIV BATH,SCH BIOL & BIOCHEM,BATH BA2 7AY,AVON,ENGLAND
关键词
D O I
10.1016/S0040-4039(00)76910-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The regioselective demethylation of aconitine has been achieved with Lewis acids. Me(3)SiI afforded first 18-O-desmethyl- and then 16,18-di-O-desmethylaconitine, but AlCl3/NaI gave 16-O-desmethylaconitine first. The acetate and benzoate esters survived throughout these procedures. Aconitine decomposed on treatment with BBr3.
引用
收藏
页码:3367 / 3370
页数:4
相关论文
共 28 条
[1]   CHASMANINE AND ITS STRUCTURE [J].
ACHMATOW.O ;
TSUDA, Y ;
MARION, L ;
OKAMOTO, T ;
NATSUME, M ;
CHANG, HH ;
KAJIMA, K .
CANADIAN JOURNAL OF CHEMISTRY, 1965, 43 (04) :825-&
[2]   A CHIRAL SYNTHESIS OF D-MYO-INOSITOL 1-PHOSPHATE STARTING FROM L-QUEBRACHITOL [J].
AKIYAMA, T ;
TAKECHI, N ;
OZAKI, S ;
SHIOTA, K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (02) :366-372
[3]  
Benn M., 1983, ALKALOIDS CHEM BIOL, V1, P153
[4]   DITERPENOID ALKALOIDS FROM DELPHINIUM-WINKLERIANUM [J].
CHEN, YZ ;
WU, AG .
PHYTOCHEMISTRY, 1990, 29 (03) :1016-1019
[5]  
DESAI HK, 1985, HETEROCYCLES, V23, P2483
[6]   METHANOLYSIS OF THE C-8 ACETOXYL GROUP IN ACONITINE-TYPE ALKALOIDS - A PARTIAL SYNTHESIS OF HOKBUSINE-A [J].
DESAI, HK ;
JOSHI, BS ;
ROSS, SA ;
PELLETIER, SW .
JOURNAL OF NATURAL PRODUCTS, 1989, 52 (04) :720-725
[7]   REVISED C-13 NMR ASSIGNMENTS FOR NORDITERPENOID ALKALOIDS WITH 7,8-METHYLENEDIOXY AND 10-BETA-OH GROUPS [J].
DESAI, HK ;
PELLETIER, SW .
JOURNAL OF NATURAL PRODUCTS, 1993, 56 (07) :1140-1147
[8]  
DESAI HK, 1993, HETEROCYCLES, V36, P1081
[9]   ISODELECTINE - A NEW NORDITERPENOID ALKALOID FROM DELPHINIUM-VESTITUM [J].
DESAI, HK ;
ELSOFANY, RH ;
PELLETIER, SW .
JOURNAL OF NATURAL PRODUCTS, 1990, 53 (06) :1606-1608
[10]   ISOLATION AND IDENTIFICATION OF 4 NORDITERPENOID ALKALOIDS FROM PROCESSED AND UNPROCESSED ROOT TUBERS OF ACONITUM-FEROX [J].
HANUMAN, JB ;
KATZ, A .
JOURNAL OF NATURAL PRODUCTS, 1993, 56 (06) :801-809