Novel assembly of cyclic ethers by coupling α-chlorosulfides and alcohols

被引：48

作者：

Inoue, M ^{[1
]}

Xing, G

Wang, X

Wang, J

Hirama, M

机构：

[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan

[2] Japan Sci & Technol Corp, JST, CREST, Sendai, Miyagi 9808578, Japan

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 20期

关键词：

D O I：

10.1021/ol026529d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A novel protocol for assembling polycyclic ethers was developed and successfully applied to the synthesis of the EFGH ring system of ciguatoxin CTX3C, A key transformation involves construction of an O,S-acetal through coupling of alpha-chlorosulfide and a secondary alcohol under mild conditions. The method is highly applicable to use with sensitive substrates and will enable the synthesis of various natural and artificial polycyclic ethers.

引用

页码：3439 / 3442

页数：4

共 63 条

[1]

Armstrong SK, 1998, J CHEM SOC PERK T 1, P371

[2] TETRAHYDROPYRAN SYNTHESIS VIA RADICAL CYCLIZATION - A SYSTEMATIC STUDY OF SUBSTITUENT EFFECTS [J].

BURKE, SD ;

RANCOURT, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (06) :2335-2336

[3]

Clark JS, 2000, ANGEW CHEM INT EDIT, V39, P372, DOI 10.1002/(SICI)1521-3773(20000117)39:2<372::AID-ANIE372>3.0.CO

[4]

2-Y

[5] 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

[6] ORGANIC-SYNTHESIS WITH ALPHA-CHLOROSULFIDES [J].

DILWORTH, BM ;

MCKERVEY, MA .

TETRAHEDRON, 1986, 42 (14) :3731-3752

[7] A short synthesis of the A/B ring systems of the Pacific ciguatoxins P-CTX-3C and dihydroxy-P-CTX-3C [J].

Eriksson, L ;

Guy, S ;

Perlmutter, P ;

Lewis, R .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (22) :8396-8398

[8] CATALYTIC RING-CLOSING METATHESIS OF FUNCTIONALIZED DIENES BY A RUTHENIUM CARBENE COMPLEX [J].

FU, GC ;

NGUYEN, ST ;

GRUBBS, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (21) :9856-9857

[9] Asymmetric synthesis of the A-ring part of ciguatoxin by the strategy based on diastereoselective hydroboration and ring closing metathesis [J].

Fujiwara, K ;

Tanaka, H ;

Murai, A .

CHEMISTRY LETTERS, 2000, (06) :610-611

[10]

Fujiwara K, 2001, SYNLETT, P691

← 1 2 3 4 5 6 7 →