Total syntheses of marine polycyclic ethers

被引:341
作者
Nakata, T [1 ]
机构
[1] Tokyo Univ Sci, Dept Chem, Shinjuku Ku, Tokyo 1628601, Japan
关键词
D O I
10.1021/cr040627q
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A review of the total synthesis of marine polycyclic ethers by several synthetic organic chemists who have extensively studied the development of new strategies and efficient methodologies for the construction of ether rings and their application is presented. The intensive endeavors of these chemists have accumulated many efficient strategies and useful methods for construction of various types of polycycling ether ring systems. In addition to the total landmark syntheses of brevetoxin-B (BTX-B) and BTX-A, recent remarkable progress in synthetic organic chemistry has completed efficient syntheses of marine polyethers, including BTX-B, ciguatoxin CTX3C, gambierol and gymnocin-A.
引用
收藏
页码:4314 / 4347
页数:34
相关论文
共 176 条
[71]  
2-S
[72]   EFFICACIOUS MODIFICATION OF THE MITSUNOBU REACTION FOR INVERSIONS OF STERICALLY HINDERED SECONDARY ALCOHOLS [J].
MARTIN, SF ;
DODGE, JA .
TETRAHEDRON LETTERS, 1991, 32 (26) :3017-3020
[73]   Stereoselective synthesis of tetrahydropyran and oxepane systems by the endo-cyclization of hydroxy styrylepoxides [J].
Matsukura, H ;
Morimoto, M ;
Koshino, H ;
Nakata, T .
TETRAHEDRON LETTERS, 1997, 38 (31) :5545-5548
[74]   Total synthesis of brevetoxin-B [J].
Matsuo, G ;
Kawamura, K ;
Hori, N ;
Matsukura, H ;
Nakata, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (44) :14374-14376
[75]   Stereoselective syntheses of trans-fused 6,6-and 6,7-membered ether ring systems having an angular methyl group based on SmI2-induced reductive intramolecular cyclization [J].
Matsuo, G ;
Hori, N ;
Nakata, T .
TETRAHEDRON LETTERS, 1999, 40 (50) :8859-8862
[76]   Synthetic studies on brevetoxin-B. Part 2. Stereoselective synthesis of the EFG-ring system [J].
Matsuo, G ;
Hori, N ;
Matsukura, H ;
Nakata, T .
TETRAHEDRON LETTERS, 2000, 41 (40) :7677-7680
[77]   The organoselenium-mediated reduction of alpha,beta-epoxy ketones, alpha,beta-epoxy esters, and their congeners to beta-hydroxy carbonyl compounds: Novel methodologies for the synthesis of aldols and their analogues [J].
Miyashita, M ;
Suzuki, T ;
Hoshino, M ;
Yoshikoshi, A .
TETRAHEDRON, 1997, 53 (37) :12469-12486
[78]   LANTHANIDES IN ORGANIC-SYNTHESIS .8. 1,3-ASYMMETRIC INDUCTION IN INTRAMOLECULAR REFORMATSKY-TYPE REACTIONS PROMOTED BY SAMARIUM DIIODIDE [J].
MOLANDER, GA ;
ETTER, JB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (21) :6556-6558
[79]   A new strategy for the reiterative synthesis of trans-fused tetrahydropyrans via alkylation of oxiranyl anion and 6-endo cyclization [J].
Mori, Y ;
Yaegashi, K ;
Furukawa, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (34) :8158-8159
[80]   Reiterative synthesis of trans-fused polytetrahydropyrans using the oxiranyl anion [J].
Mori, Y .
CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (06) :849-852