The Chemical Synthesis of Tetrodoxin: An Ongoing Quest

被引：33

作者：

Chau, Jaclyn ^{[1
]}

Ciufolini, Marco A. ^{[1
]}

机构：

[1] Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z1, Canada

来源：

MARINE DRUGS | 2011年 / 9卷 / 10期

基金：

加拿大健康研究院;

关键词：

tetrodotoxin; synthesis; nitrenes; hypervalent iodine compounds; INTERMEDIATES POTENTIALLY USEFUL; ASYMMETRIC TOTAL-SYNTHESIS; EFFICIENT TOTAL-SYNTHESIS; OXIDATIVE AMIDATION; NATURAL-PRODUCTS; STEREOCONTROLLED SYNTHESIS; RADICAL CYCLIZATION; CARBOHYDRATE-DERIVATIVES; SUGAR KETONITRONES; UNNATURAL ANALOG;

D O I：

10.3390/md9102046

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

This contribution reviews all the synthetic work on tetrodotoxin that has appeared in the literature through June 2011.

引用

页码：2046 / 2074

页数：29

共 87 条

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

Akai, Shoji ;

Seki, Hidehito ;

Sugita, Naoki ;

Kogure, Tomokazu ;

Nishizawa, Naoki ;

Suzuki, Katsuhiko ;

Nakamura, Yutaka ;

Kajihara, Yasuhiro ;

Yoshimura, Juji ;

Sato, Ken-ichi .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2010, 83 (03) :279-287

[2] CARBOHYDRATES TO CARBOCYCLES - SYNTHESIS OF THE DENSELY FUNCTIONALIZED CARBOCYCLIC CORE OF TETRODOTOXIN BY RADICAL CYCLIZATION OF AN ANHYDRO SUGAR PRECURSOR [J].

ALONSO, RA ;

BURGEY, CS ;

RAO, BV ;

VITE, GD ;

VOLLERTHUN, R ;

ZOTTOLA, MA ;

FRASERREID, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) :6666-6672

[3]

[Anonymous], MOD SYN MET

[4] Stereocontrolled synthesis of (-)-5,11-dideoxytetrodotoxin [J].

Asai, M ;

Nishikawa, T ;

Ohyabu, N ;

Yamamoto, N ;

Isobe, M .

TETRAHEDRON, 2001, 57 (21) :4543-4558

[5] TOTAL SYNTHESIS OF KUANONIAMINES AND DERCITINS [J].

BISHOP, MJ ;

CIUFOLINI, MA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (25) :10081-10082

[6] Hypervalent iodine oxidation of indolic 2-oxazolines [J].

Braun, NA ;

Bray, JD ;

Ciufolini, MA .

TETRAHEDRON LETTERS, 1999, 40 (27) :4985-4988

[7] New oxidative transformations of phenolic and indolic oxazolines: An avenue to useful azaspirocyclic building blocks [J].

Braun, NA ;

Ousmer, M ;

Bray, JD ;

Bouchu, D ;

Peters, K ;

Peters, EM ;

Ciufolini, MA .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (14) :4397-4408

[8] Synthesis of spirolactams from tyrosine amides and related substances [J].

Braun, NA ;

Ciufolini, MA ;

Peters, K ;

Peters, EM .

TETRAHEDRON LETTERS, 1998, 39 (26) :4667-4670

[9] 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

[10] A Cascade Annulation Based Convergent Approach to Racemic Tetrodotoxin [J].

Cagide-Fagin, Fernando ;

Alonso, Ricardo .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (35) :6741-6747

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