Synthesis of (-)-histrionicotoxin by a tandem process

被引:94
作者
Williams, GM
Roughley, SD
Davies, JE
Holmes, AB
Adams, JP
机构
[1] Univ Cambridge, Dept Chem, Chem Lab, Cambridge CB2 1EW, England
[2] Glaxo Wellcome Res & Dev Ltd, Med Res Ctr, Stevenage SG1 2NY, Herts, England
关键词
D O I
10.1021/ja990138l
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
引用
收藏
页码:4900 / 4901
页数:2
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共 26 条
[1]   MODEL STUDIES ON THE ACTIVE-SITE OF CYTOCHROME-P-450 - AN FEII PORPHYRIN CARRYING A STRAPPED THIOLATE LIGAND [J].
BATTERSBY, AR ;
HOWSON, W ;
HAMILTON, AD .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (21) :1266-1268
[2]   A TOTAL SYNTHESIS OF D,1-HISTRIONICOTOXIN [J].
CAREY, SC ;
ARATANI, M ;
KISHI, Y .
TETRAHEDRON LETTERS, 1985, 26 (48) :5887-5890
[3]  
CONGREVE MS, 1993, SYNLETT, P663
[4]   Regio- and diastereoselective 1,3-dipolar cycloaddition of imidazoline 3-oxides to styrene [J].
Coskun, N ;
Ay, M .
HETEROCYCLES, 1998, 48 (03) :537-544
[5]   HISTRIONICOTOXINS - ROENTGEN-RAY ANALYSIS OF NOVEL ALLENIC AND ACETYLENIC SPIROALKALOIDS ISOLATED FROM A COLOMBIAN FROG, DENDROBATES-HISRIONICUS [J].
DALY, JW ;
KARLE, I ;
MYERS, CW ;
TOKUYAMA, T ;
WATERS, JA ;
WITKOP, B .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1971, 68 (08) :1870-&
[6]   N-alkenyl nitrone dipolar cycloaddition routes to piperidines and indolizidines .8. the scope of tandem reactions involving hydroxylamine-alkyne cyclisations [J].
Davison, EC ;
Forbes, IT ;
Holmes, AB ;
Warner, JA .
TETRAHEDRON, 1996, 52 (35) :11601-11624
[7]   N-ALKENYL NITRONE DIPOLAR CYCLOADDITION ROUTES TO PIPERIDINES AND INDOLIZIDINES .7. HYDROXYLAMINE ALKYNE CYCLIZATIONS - FORMATION OF CYCLIC NITRONES AND APPLICATION TO THE SYNTHESIS OF THE PROPOSED STRUCTURE FOR (+/-)-ACACIALACTAM [J].
FOX, ME ;
HOLMES, AB ;
FORBES, IT ;
THOMPSON, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (23) :3379-3395
[8]   PALLADIUM(II)-CATALYZED CASCADE CYCLIZATION CYCLOADDITION REACTIONS OF ALKENYL OXIMES [J].
FREDERICKSON, M ;
GRIGG, R ;
MARKANDU, J ;
REDPATH, J .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (19) :2225-2226
[9]   REGIOCONTROLLED AND STEREOCONTROLLED SYNTHESIS OF ALLENIC AND ACETYLENIC DERIVATIVES - ORGANOTITANIUM AND BORON REAGENTS [J].
FURUTA, K ;
ISHIGURO, M ;
HARUTA, R ;
IKEDA, N ;
YAMAMOTO, H .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1984, 57 (10) :2768-2776
[10]   PROBES FOR A REGULATORY SITE ON THE NICOTINIC ACETYLCHOLINE RECEPTOR-CHANNEL - SYNTHESIS OF (+/-)-7-DEBUTYLPERHYDROHISTRIONICOTOXIN, (+--)-2-DEPENTYL-7-DEBUTYLPERHYDROHISTRIONICOTOXIN, AND THEIR ANALOGS [J].
GESSNER, W ;
TAKAHASHI, K ;
WITKOP, B ;
BROSSI, A ;
ALBUQUERQUE, EX .
HELVETICA CHIMICA ACTA, 1985, 68 (01) :49-55