Chemoenzymatic Synthesis of Advanced Intermediates for Formal Total Syntheses of Tetrodotoxin

被引：20

作者：

Baidilov, Daler ^{[1
,2
]}

Rycek, Lukas ^{[1
,2
]}

Trant, John F. ^{[1
,2
]}

Froese, Jordan ^{[1
,2
]}

Murphy, Brennan ^{[1
,2
]}

Hudlicky, Tomas ^{[1
,2
]}

机构：

[1] Brock Univ, Dept Chem, 1812 Sir Isaac Brock Way, St Catharines, ON L2S 3A1, Canada

[2] Brock Univ, Ctr Biotechnol, 1812 Sir Isaac Brock Way, St Catharines, ON L2S 3A1, Canada

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 34期

基金：

加拿大自然科学与工程研究理事会; 加拿大创新基金会;

关键词：

chemoenzymatic synthesis; formal synthesis; hydride shift; tetrodotoxin; total synthesis; OPTICALLY-ACTIVE TETRODOTOXIN; BASE-CATALYZED DECOMPOSITION; TO-ISOCYANATE REARRANGEMENT; EFFICIENT TOTAL-SYNTHESIS; WITTIG REACTION; STEREOSELECTIVE-SYNTHESIS; NUCLEOPHILIC GROUPS; PHOSPHONIUM YLIDE; D-GLUCOSE; (-)-TETRODOTOXIN;

D O I：

10.1002/anie.201804602

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Advanced intermediates for the syntheses of tetrodotoxin reported by the groups of Fukuyama, Alonso, and Sato were prepared. Key steps include the toluene dioxygenase mediated dihydroxylation of either iodobenzene or benzyl acetate. The resulting diene diols were transformed into Fukuyama's intermediate in six steps, into Alonso's intermediate in nine steps, and into Sato's intermediate in ten steps.

引用

页码：10994 / 10998

页数：5

共 61 条

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