REGIOSELECTIVE ANTHRANOYLATION OF DEMETHYLATED ACONITINE - NOVEL ANALOGS OF ACONITINE, INULINE AND METHYLLYCACONITINE

被引:15
作者
HARDICK, DJ
BLAGBROUGH, IS
WONNACOTT, S
POTTER, BVL
机构
[1] UNIV BATH,SCH PHARM & PHARMACOL,DEPT MED CHEM,BATH BA2 7AY,AVON,ENGLAND
[2] UNIV BATH,SCH BIOL & BIOCHEM,BATH BA2 7AY,AVON,ENGLAND
关键词
D O I
10.1016/S0040-4039(00)76911-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The regioselective acylation of 18-O-desmethylaconitine has been achieved with isatoic anhydride to afford the corresponding anthranilate ester, an analogue of inuline. The aniline nitrogen was then incorporated into an S-methylsuccinimide moiety, to afford a novel methyllycaconitine/aconitine hybrid alkaloid.
引用
收藏
页码:3371 / 3374
页数:4
相关论文
共 14 条
  • [1] NEW METHOD FOR DEOXYGENATION OF SECONDARY ALCOHOLS
    BARTON, DHR
    MCCOMBIE, SW
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16): : 1574 - 1585
  • [2] Benn M., 1983, ALKALOIDS CHEM BIOL, V1, P153
  • [3] BLAGBROUGH IS, 1994, TETRAHEDRON LETT, P35
  • [4] CONVERSION OF 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSE (N-ACETYLGLUCOSAMINE) INTO 2-ACETAMIDO-2-DEOXY-BETA-D-GALACTOPYRANOSE (N-ACETYLGALACTOSAMINE) USING A BIOTRANSFORMATION TO GENERATE A SELECTIVELY DEPROTECTED SUBSTRATE FOR SN2 INVERSION
    CHAPLIN, D
    CROUT, DHG
    BORNEMANN, S
    HUTCHINSON, DW
    KHAN, R
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (02): : 235 - 237
  • [5] C-13 NUCLEAR-MAGNETIC-RESONANCE SPECTROSCOPY IN THE ELUCIDATION OF STRUCTURES OF DITERPENOID ALKALOIDS
    JOSHI, BS
    WUNDERLICH, JK
    PELLETIER, SW
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (01): : 99 - 103
  • [6] DEOXYGENATION REACTIONS OF C-19-DITERPENOID ALKALOIDS
    KULANTHAIVEL, P
    PELLETIER, SW
    [J]. TETRAHEDRON, 1988, 44 (14) : 4313 - 4320
  • [7] SYNTHESIS OF INOSITOL PHOSPHATES
    MEEK, JL
    DAVIDSON, F
    HOBBS, FW
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (07) : 2317 - 2318
  • [8] Pelletier S.W., 1991, ALKALOIDS CHEM BIOL, P297, DOI [10.1007/978-1-4612-3006-9_3, DOI 10.1007/978-1-4612-3006-9]
  • [9] PELLETIER SW, 1991, HETEROCYCLES, V32, P1307
  • [10] Pelletier SW., 1984, ALKALOIDS CHEM BIOL, P205