Stereoselective synthesis of the fully functionalized HIJ-ring framework of ciguatoxin

被引：22

作者：

Baba, T ^{[1
]}

Takai, S ^{[1
]}

Sawada, N ^{[1
]}

Isobe, M ^{[1
]}

机构：

[1] Nagoya Univ, Sch Bioagr Sci, Organ Chem Lab, Nagoya, Aichi, Japan

来源：

SYNLETT | 2004年 / 04期

关键词：

alkyne cobalt complexes; reductive decomplexation; medium sized ring closure reaction; intramolecular 1,4-addition reaction; ciguatoxin;

D O I：

10.1055/s-2004-817769

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient convergent synthetic route to construct the HIJ-ring system of ciguatoxin was achieved via stereo controlled eight-membered ring formation by using acetylene cobalt complex and subsequent six-membered ring formation through intramolecular 1,4-addition reaction.

引用

页码：603 / 608

页数：6

共 41 条

[1] Medicinal chemistry of neuronal voltage-gated sodium channel blockers [J].

Anger, T ;

Madge, DJ ;

Mulla, M ;

Riddall, D .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (02) :115-137

[2] Synthesis of the JKLM-ring fragment of ciguatoxin [J].

Baba, T ;

Huang, G ;

Isobe, M .

TETRAHEDRON, 2003, 59 (35) :6851-6872

[3] ALPHA-CHLORO-ALPHA-TRIMETHYLSILYL CARBANION, A REAGENT FOR HOMOLOGATION OF KETONES AND ALDEHYDES VIA ALPHA,BETA-EPOXYSILANES [J].

BURFORD, C ;

COOKE, F ;

EHLINGER, E ;

MAGNUS, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (13) :4536-4537

[4] Ciguatoxins and brevetoxins, neurotoxic polyether compounds active on sodium channels [J].

Dechraoui, MY ;

Naar, J ;

Pauillac, S ;

Legrand, AM .

TOXICON, 1999, 37 (01) :125-143

[5]

Fernández-Megía E, 2000, SYNLETT, P455

[6] CIGUATERA IN AUSTRALIA - OCCURRENCE, CLINICAL-FEATURES, PATHOPHYSIOLOGY AND MANAGEMENT [J].

GILLESPIE, NC ;

LEWIS, RJ ;

PEARN, JH ;

BOURKE, ATC ;

HOLMES, MJ ;

BOURKE, JB ;

SHIELDS, WJ .

MEDICAL JOURNAL OF AUSTRALIA, 1986, 145 (11-12) :584-590

[7] Total synthesis of ciguatoxin CTX3C [J].

Hirama, M ;

Oishi, T ;

Uehara, H ;

Inoue, M ;

Maruyama, M ;

Guri, H ;

Satake, M .

SCIENCE, 2001, 294 (5548) :1904-1907

[8] Reductive decomplexation of biscobalthexacarbonyl acetylenes into olefins [J].

Hosokawa, S ;

Isobe, M .

TETRAHEDRON LETTERS, 1998, 39 (17) :2609-2612

[9] Practical total synthesis of ciguatoxin CTX3C by improved protective group strategy [J].

Inoue, M ;

Uehara, H ;

Maruyama, M ;

Hirama, M .

ORGANIC LETTERS, 2002, 4 (25) :4551-4554

[10]

ISOBE M, 1994, SYNLETT, P916

← 1 2 3 4 5 →