Progress toward the total synthesis of ciguatoxins: A convergent synthesis of the FGHIJKLM ring fragment

被引：56

作者：

Takakura, H

Sasaki, M ^{[1
]}

Honda, S

Tachibana, K

机构：

[1] Tohoku Univ, Grad Sch Life Sci, Lab Biostruct Chem, Aoba Ku, Sendai, Miyagi 9818555, Japan

[2] Univ Tokyo, Grad Sch Sci, Dept Chem, Tokyo 1130033, Japan

[3] Japan Sci & Technol Corp, JST, CREST, Tokyo 1130033, Japan

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 16期

关键词：

D O I：

10.1021/ol026306n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A highly convergent synthetic route to the FGHIJKLM ring fragment of ciguatoxins has been developed, which relied on extensive use of the B-alkyl Suzuki-Miyaura coupling reaction.

引用

页码：2771 / 2774

页数：4

共 62 条

[1] USEFUL DESIGNS IN THE SYNTHESIS OF TRANS-FUSED POLYETHER TOXINS [J].

ALVAREZ, E ;

CANDENAS, ML ;

PEREZ, R ;

RAVELO, JL ;

MARTIN, JD .

CHEMICAL REVIEWS, 1995, 95 (06) :1953-1980

[2] A MILD AND STEREOSPECIFIC CONVERSION OF VICINAL DIOLS INTO OLEFINS VIA 2-METHOXY-1,3-DIOXOLANE DERIVATIVES [J].

ANDO, M ;

OHHARA, H ;

TAKASE, K .

CHEMISTRY LETTERS, 1986, (06) :879-882

[3]

BIDARD JN, 1984, J BIOL CHEM, V259, P8353

[4] Synthesis of a ring F building block for the ciguatoxins [J].

Bond, S ;

Perlmutter, P .

TETRAHEDRON, 2002, 58 (10) :1779-1787

[5] Synthesis and biological studies of flexible brevetoxin/ciguatoxin models with marked conformational preference [J].

Candenas, ML ;

Pinto, FM ;

Cintado, CG ;

Morales, EQ ;

Brouard, I ;

Díaz, MT ;

Rico, M ;

Rodríguez, E ;

Rodríguez, RM ;

Pérez, R ;

Pérez, RL ;

Martín, JD .

TETRAHEDRON, 2002, 58 (10) :1921-1942

[6]

Chemler SR, 2001, ANGEW CHEM INT EDIT, V40, P4544, DOI 10.1002/1521-3773(20011217)40:24<4544::AID-ANIE4544>3.0.CO

[7]

2-N

[8] 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

[9]

Fujiwara K, 2001, SYNLETT, P691

[10] Synthetic studies on a marine polyether toxin, gambierol:: stereoselective synthesis of the FGH ring system via B-alkyl Suzuki coupling [J].

Fuwa, H ;

Sasaki, M ;

Tachibana, K .

TETRAHEDRON LETTERS, 2000, 41 (43) :8371-8375

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