Convergent synthesis of the BCDE-ring part of ciguatoxin

被引：32

作者：

Fujiwara, K ^{[1
]}

Koyama, Y ^{[1
]}

Kawai, K ^{[1
]}

Tanaka, H ^{[1
]}

Murai, A ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Sci, Div Chem, Sapporo, Hokkaido 0600810, Japan

来源：

SYNLETT | 2002年 / 11期

关键词：

heterocycles; stereoselective synthesis; natural products; polyethers; polycycles;

D O I：

10.1055/s-2002-34904

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The BCDE-ring part of ciguatoxin has been convergently synthesized by a sequence of reactions involving coupling of the E-ring part having a Z-enal group with the B-ring part as an acyl anion equivalent, selective removal of a p-bromobenzyl protective group using Miyaura's conditions, and reductive cyclization.

引用

页码：1835 / 1838

页数：4

共 62 条

[31] STRUCTURES OF CIGUATOXIN AND ITS CONGENER [J].

MURATA, M ;

LEGRAND, AM ;

ISHIBASHI, Y ;

YASUMOTO, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (24) :8929-8931

[32] STRUCTURES AND CONFIGURATIONS OF CIGUATOXIN FROM THE MORAY EEL GYMNOTHORAX-JAVA']JAVANICUS AND ITS LIKELY PRECURSOR FROM THE DINOFLAGELLATE GAMBIERDISCUS-TOXICUS [J].

MURATA, M ;

LEGRAND, AM ;

ISHIBASHI, Y ;

FUKUI, M ;

YASUMOTO, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) :4380-4386

[33]

Nicolaou KC, 1996, ANGEW CHEM INT EDIT, V35, P589

[34] SYNTHETIC STUDIES ON THE DIOXEPANE REGION OF BREVETOXIN-B - NEW SYNTHETIC TECHNOLOGY FOR THE CONSTRUCTION OF OXEPANES AND SYNTHESIS OF A MODEL FOR THE CDEF RING SKELETON OF BREVETOXIN-B [J].

NICOLAOU, KC ;

HWANG, CK ;

NUGIEL, DA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (11) :4136-4137

[35] 2 INTERCHANGEABLE FORMS OF CIGUATOXIN [J].

NUKINA, M ;

KOYANAGI, LM ;

SCHEUER, PJ .

TOXICON, 1984, 22 (02) :169-176

[36]

OGURA K, 1972, TETRAHEDRON LETT, P2681

[37] A very short route to the functionalized A-ring moiety of ciguatoxin [J].

Oguri, H ;

Tanaka, S ;

Oishi, T ;

Hirama, M .

TETRAHEDRON LETTERS, 2000, 41 (06) :975-978

[38]

Oishi T, 2001, SYNLETT, P952

[39]

Oishi T, 1997, SYNLETT, P980

[40] Convergent synthesis of the trans-fused 6-n-6-6 (n = 7-10) tetracyclic ether system based on a ring-closing metathesis reaction [J].

Oishi, T ;

Nagumo, Y ;

Hirama, M .

CHEMICAL COMMUNICATIONS, 1998, (09) :1041-1042

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