Total Synthesis of (-)-Tetrodotoxin from D-Glucose: A New Route to Multi-Functionalized Cyclitol Employing the Ferrier(II) Reaction toward (-)-Tetrodotoxin

被引：30

作者：

Akai, Shoji ^{[1
]}

Seki, Hidehito ^{[1
]}

Sugita, Naoki ^{[1
]}

Kogure, Tomokazu ^{[1
]}

Nishizawa, Naoki ^{[1
]}

Suzuki, Katsuhiko ^{[1
]}

Nakamura, Yutaka ^{[1
]}

Kajihara, Yasuhiro ^{[1
]}

Yoshimura, Juji ^{[2
]}

Sato, Ken-ichi ^{[1
]}

机构：

[1] Kanagawa Univ, Fac Engn, Kanagawa Ku, Yokohama, Kanagawa 2218686, Japan

[2] Iwaki Meisei Univ, Coll Sci & Engn, Dept Basic Sci, Iwaki, Fukushima 9708551, Japan

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 2010年 / 83卷 / 03期

关键词：

OPTICALLY-ACTIVE TETRODOTOXIN; EFFICIENT TOTAL-SYNTHESIS; ASYMMETRIC TOTAL-SYNTHESIS; PUFFER FISH; STEREOSELECTIVE-SYNTHESIS; DERIVATIVES; SUGARS; TOXIN;

D O I：

10.1246/bcsj.20090194

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Total synthesis of (-)-tetrodotoxin (TTX) from D-glucose is described. As a critical transformation step or synthesizing TTX, a key multi-functionalized cyclitol was prepared from D-glucose employing the Ferrier(II) reaction. Stereospecific introduction of three functionalized branched chains were achieved via Peterson olefination and spiro alpha-chloroepoxidation of the corresponding carbonyl derivatives.

引用

页码：279 / 287

页数：9

共 39 条

[1] BIOMIMETIC SYNTHESIS OF ENANTIOMERICALLY PURE D-MYO-INOSITOL DERIVATIVES [J].

BENDER, SL ;

BUDHU, RJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (26) :9883-9885

[2] Armed disarmed effects and adamantyl expansion of some caged tricyclic acetals en route to tetrodotoxin [J].

Burgey, CS ;

Vollerthun, R ;

FraserReid, B .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (05) :1609-1618

[3] Marine toxins and nonmarine toxins: Convergence or symbiotic organisms [J].

Daly, JW .

JOURNAL OF NATURAL PRODUCTS, 2004, 67 (08) :1211-1215

[4] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287

[5] Some approaches to glycosylated versions of methyl β-acarviosin [J].

Fairweather, JK ;

McDonough, MJ ;

Stick, RV ;

Tilbrook, DMG .

AUSTRALIAN JOURNAL OF CHEMISTRY, 2004, 57 (03) :197-205

[6] Formation of five- and six-membered carbocycles with nitrogenated tetrasubstituted carbons by radical addition-carbocyclization of alkynyl ketoxime ethers [J].

Fernandez-Gonzalez, Marta ;

Alonso, Ricardo .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (18) :6767-6775

[7] THE CONVERSION OF CARBOHYDRATE-DERIVATIVES INTO FUNCTIONALIZED CYCLOHEXANES AND CYCLOPENTANES [J].

FERRIER, RJ ;

MIDDLETON, S .

CHEMICAL REVIEWS, 1993, 93 (08) :2779-2831

[8] BRANCHED-CHAIN SUGARS .5. STEREOSELECTIVE SYNTHESIS OF 3-C-METHYL-D-GLUCOSES AND 5-C-METHYL-D-GLUCOSES, AND 5-C-METHYL-L-IDOSE DERIVATIVES [J].

FUNABASHI, M ;

SATO, H ;

YOSHIMURA, J .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1976, 49 (03) :788-790

[9] TETRODOTOXIN [J].

GOTO, T ;

KISHI, Y ;

TAKAHASH.S ;

HIRATA, Y .

TETRAHEDRON, 1965, 21 (08) :2059-&

[10] A stereoselective synthesis of (-)-tetrodotoxin [J].

Hinman, A ;

Du Bois, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (38) :11510-11511

← 1 2 3 4 →