Total synthesis of polyamine amide spider toxin argiotoxin-636 by a practical reductive alkylation strategy

被引:22
作者
Blagbrough, IS
Moya, E
机构
[1] Department of Medicinal Chemistry, School of Pharmacy and Pharmacology, University of Bath, Bath, BA2 7AY, Claverton Down
基金
英国惠康基金; 英国医学研究理事会;
关键词
D O I
10.1016/0040-4039(95)01994-S
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reductive alkylation is a practical strategy for a total synthesis of spider toxin argiotoxin-636, a polyamine amide which is a selective glutamate receptor antagonist and may have potential as a neuroprotective agent. Central to this synthesis are a Swern oxidation and a reductive alkylation.
引用
收藏
页码:9393 / 9396
页数:4
相关论文
共 23 条
[1]   STRUCTURES AND BIOLOGICAL-ACTIVITIES OF 3 SYNAPTIC ANTAGONISTS FROM ORB WEAVER SPIDER VENOM [J].
ADAMS, ME ;
CARNEY, RL ;
ENDERLIN, FE ;
FU, ET ;
JAREMA, MA ;
LI, JP ;
MILLER, CA ;
SCHOOLEY, DA ;
SHAPIRO, MJ ;
VENEMA, VJ .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1987, 148 (02) :678-683
[2]   LARGE-SCALE PREPARATION OF (2S,3S)-N-BOC-3-AMINO-1,2-EPOXY-4-PHENYLBUTANE - A KEY BUILDING-BLOCK FOR HIV-PROTEASE INHIBITORS [J].
BEAULIEU, PL ;
WERNIC, D ;
DUCEPPE, JS ;
GUINDON, Y .
TETRAHEDRON LETTERS, 1995, 36 (19) :3317-3320
[3]   POLYAMINE AMIDE TOXINS AS PHARMACOLOGICAL TOOLS AND PHARMACEUTICAL AGENTS [J].
BLAGBROUGH, IS ;
USHERWOOD, PNR .
PROCEEDINGS OF THE ROYAL SOCIETY OF EDINBURGH SECTION B-BIOLOGICAL SCIENCES, 1992, 99 :67-81
[4]   SYNTHESIS AND ASSAY OF HYBRID ANALOGS OF ARGIOTOXIN-636 AND PHILANTHOTOXIN-433 - GLUTAMATE-RECEPTOR ANTAGONISTS [J].
CHOI, SK ;
NAKANISHI, K ;
USHERWOOD, PNR .
TETRAHEDRON, 1993, 49 (26) :5777-5790
[5]   ARGIOTOXIN636 INHIBITS NMDA-ACTIVATED ION CHANNELS EXPRESSED IN XENOPUS OOCYTES [J].
DRAGUHN, A ;
JAHN, W ;
WITZEMANN, V .
NEUROSCIENCE LETTERS, 1991, 132 (02) :187-190
[6]  
GRISHIN EV, 1986, BIOORG KHIM+, V12, P1121
[7]  
HAMADA Y, 1982, CHEM PHARM BULL, V30, P1921
[8]   ARGIOTOXIN DETECTS MOLECULAR DIFFERENCES IN AMPA RECEPTOR CHANNELS [J].
HERLITZE, S ;
RADITSCH, M ;
RUPPERSBERG, JP ;
JAHN, W ;
MONYER, H ;
SCHOEPFER, R ;
WITZEMANN, V .
NEURON, 1993, 10 (06) :1131-1140
[9]   THE TOTAL SYNTHESIS OF ARGIOTOXIN-636, ARGIOTOXIN-659 AND ARGIOTOXIN-673 [J].
JASYS, VJ ;
KELBAUGH, PR ;
NASON, DM ;
PHILLIPS, D ;
SACCOMANO, NA ;
VOLKMANN, RA .
TETRAHEDRON LETTERS, 1988, 29 (48) :6223-6226
[10]   1,3-DIYL TRAPPING REACTIONS - FUNDAMENTAL INVESTIGATIONS WITH APPLICATION TO THE SYNTHESIS OF LINEARLY FUSED TRICYCLOPENTANOIDS [J].
LITTLE, RD ;
MULLER, GW ;
VENEGAS, MG ;
CARROLL, GL ;
BUKHARI, A ;
PATTON, L ;
STONE, K .
TETRAHEDRON, 1981, 37 (25) :4371-4383