Studies into the synthesis of a sub-unit of the neurotoxic alkaloid methyllycaconitine

被引:27
作者
Baillie, LC
Bearder, JR
Li, WS
Sherringham, JA
Whiting, DA
机构
[1] Univ Nottingham, Dept Chem, Nottingham NG7 2RD, England
[2] Shell Thornton Res Ctr, Chester CH1 35H, Cheshire, England
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 24期
关键词
D O I
10.1039/a807760f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A potentially toxophoric subunit of methyllycaconitine has been synthesised from penta-1,4-dien-3-ol as the mixture of diastereomers ta and 2b, in 14 steps and 5% overall yield.
引用
收藏
页码:4047 / 4055
页数:9
相关论文
共 30 条
[1]   CYCLOADDITION OF 5-SUBSTITUTED 1-PYRROLINE 1-OXIDE AND CONVERSION OF THE NITRONE CYCLOADDUCTS INTO CIS-2,5-DISUBSTITUTED AND TRANS-2,5-DISUBSTITUTED PYRROLIDINES [J].
ALI, SA ;
WAZEER, MIM .
TETRAHEDRON, 1993, 49 (20) :4339-4354
[2]  
Arneric S. P., 1996, EXPERT OPIN INV DRUG, V5, P79, DOI [10.1517/13543784.5.1.79, DOI 10.1517/13543784.5.1.79]
[3]   POTENTIAL TREATMENT OF ALZHEIMER-DISEASE USING CHOLINERGIC CHANNEL ACTIVATORS (CHCAS) WITH COGNITIVE ENHANCEMENT, ANXIOLYTIC-LIKE, AND CYTOPROTECTIVE PROPERTIES [J].
ARNERIC, SP ;
SULLIVAN, JP ;
DECKER, MW ;
BRIONI, JD ;
BANNON, AW ;
BRIGGS, CA ;
DONNELLYROBERTS, D ;
RADEK, RJ ;
MARSH, KC ;
KYNCL, J ;
WILLIAMS, M ;
BUCCAFUSCO, JJ .
ALZHEIMER DISEASE & ASSOCIATED DISORDERS, 1995, 9 :50-61
[4]   Investigations into nicotinic acetylcholine receptor (nAChR) antagonists: synthesis of a sub-unit of methyllycaconitine [J].
Baillie, LC ;
Bearder, JR ;
Sherringham, JA ;
Whiting, DA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (18) :2687-2688
[5]   SYNTHESIS OF THE A/E/F TRICYCLIC SECTION OF THE NORDITERPENOID ALKALOID METHYLLYCACONITINE, A POTENT INHIBITOR OF NEUROTRANSMISSION [J].
BAILLIE, LC ;
BEARDER, JR ;
WHITING, DA .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (21) :2487-2488
[6]   Synthesis of the A/E/F sections of conaconitine, napelline and related diterpenoid alkaloids of the aconitine group [J].
Baillie, LC ;
Batsanov, A ;
Bearder, JR ;
Whiting, DA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (20) :3471-3478
[7]  
Benn M.H., 1983, ALKALOIDS CHEM BIOL, V1, P153
[8]   ON THE ORIGIN OF PRODUCT SELECTIVITY IN AQUEOUS DIELS-ALDER REACTIONS [J].
BRESLOW, R ;
MAITRA, U .
TETRAHEDRON LETTERS, 1984, 25 (12) :1239-1240
[9]   THE FALL AND RISE OF NEURONAL ALPHA-BUNGAROTOXIN BINDING-PROTEINS [J].
CLARKE, PBS .
TRENDS IN PHARMACOLOGICAL SCIENCES, 1992, 13 (11) :407-413
[10]   Preliminary synthetic studies of methyllycaconitine, a potent nicotinic acetylcholine receptor antagonist: Rapid syntheses of AE-bicyclic analogues [J].
Coates, PA ;
Blagbrough, IS ;
Rowan, MG ;
Pearson, DPJ ;
Lewis, T ;
Potter, BVL .
JOURNAL OF PHARMACY AND PHARMACOLOGY, 1996, 48 (02) :210-213