Convergent synthesis of an HIJK ring model of ciguatoxin via Suzuki cross-coupling reaction

被引：51

作者：

Sasaki, M ^{[1
]}

Noguchi, K ^{[1
]}

Fuwa, H ^{[1
]}

Tachibana, K ^{[1
]}

机构：

[1] Univ Tokyo, Sch Sci, Dept Chem, CREST,Japan Sci & Technol Corp,JST,Bunkyo Ku, Tokyo 1130033, Japan

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 09期

关键词：

coupling reactions; polyethers; Suzuki reactions; toxins;

D O I：

10.1016/S0040-4039(99)02307-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Convergent synthesis of HIJK ring model compound 1 of ciguatoxin is described. The present synthesis relied on a palladium-catalyzed Suzuki cross-coupling reaction between eight-membered ketene acetal phosphate 2 and seven-membered alkylborane 6. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：1425 / 1428

页数：4

共 40 条

[1] USEFUL DESIGNS IN THE SYNTHESIS OF TRANS-FUSED POLYETHER TOXINS
ALVAREZ, E
CANDENAS, ML
PEREZ, R
RAVELO, JL
MARTIN, JD
[J]. CHEMICAL REVIEWS, 1995, 95 (06) : 1953 - 1980
[2] A concise synthesis of ortho-condensed oxane-oxene, oxepene, oxocene and oxonene ring systems
Alvarez, E
Delgado, M
Diaz, MT
Liu, HX
Perez, R
Martin, JD
[J]. TETRAHEDRON LETTERS, 1996, 37 (16) : 2865 - 2868
[3] Chiral synthesis of the BC-ring system of ciguatoxin from D-glucose
Ami, E
Kishimoto, H
Ohrui, H
Meguro, H
[J]. BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1997, 61 (12) : 2019 - 2024
[4] Atsuta H, 1997, SYNLETT, P307
[5] Mirror image synthesis of left ends of ciguatoxin and gambiertoxin 4b
Hosokawa, S
Isobe, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (01) : 37 - 48
[6] Construction of fused oxonene ring and reproduction of conformational behavior shown by ring F of ciguatoxin
Inoue, M
Sasaki, M
Tachibana, K
[J]. TETRAHEDRON LETTERS, 1997, 38 (09) : 1611 - 1614
[7] A convergent synthesis of the trans-fused hexahydrooxonine ring system and reproduction of conformational behavior shown by ring F of ciguatoxin
Inoue, M
Sasaki, M
Tachibana, K
[J]. TETRAHEDRON, 1999, 55 (36) : 10949 - 10970
[8] Inoue M, 1998, ANGEW CHEM INT EDIT, V37, P965, DOI 10.1002/(SICI)1521-3773(19980420)37:7<965::AID-ANIE965>3.0.CO
[9] 2-P
[10] A convergent synthesis of the decacyclic ciguatoxin model containing the F-M ring framework
Inoue, M
Sasaki, M
Tachibana, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (26) : 9416 - 9429

← 1 2 3 4 →