Chemoenzymatic Synthesis of Hygromycin Aminocyclitol Moiety and its C2 Epimer

被引：7

作者：

Carrau, Gonzalo ^{[1
]}

Ines Bellomo, Ana ^{[2
]}

Suescun, Leopoldo ^{[3
]}

Gonzalez, David ^{[1
]}

机构：

[1] Univ Republ UdelaR, Fac Quim, Dept Quim Organ, Montevideo, Uruguay

[2] Consejo Nacl Invest Cient & Tecn CONICET, Ctr Invest Bionanociencias CIBION, Buenos Aires, DF, Argentina

[3] Univ Republ UdelaR, Fac Quim, Catedra Fis, Lab Cristalog Estado Solido & Mat,DETEMA, Montevideo, Uruguay

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 04期

关键词：

Cyclitols; Biocatalysis; Amino alcohols; Dihydroxylation; Asymmetric synthesis; BIOLOGICAL EVALUATION; ENANTIOCONTROLLED SYNTHESIS; ENANTIODIVERGENT SYNTHESIS; ANTITREPONEMAL SUBSTANCE; ASYMMETRIC-SYNTHESIS; MICROBIAL OXIDATION; (-)-HYGROMYCIN; BIOCATALYSIS; FURANOSIDE; AROMATICS;

D O I：

10.1002/ejoc.201801424

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This manuscript describes the enantioselective synthesis of the aminocyclitol moiety of the antibiotic hygromycin A in eight steps and 39 % overall yield from a non-chiral starting material. The sequence made use of an initial enzymatic step to transfer chirality to an aromatic ring and was followed by selective organic chemistry transformations (oxidation, protection, azidation, hydrolysis) of the six-membered ring in order to achieve the target. The approach is also amenable to the synthesis of other related unnatural analogues as exemplified by the synthesis of the C2 epimer of the natural aminocyclitol. All the intermediates were fully characterized, and the absolute stereochemistry assigned by spectrometric methods.

引用

页码：788 / 802

页数：15