Enantioselective Synthesis of Nabscessin C

被引：1

作者：

Yeh, Chun-Wei ^{[1
]}

Feng, Chia-Chi ^{[1
]}

Chen, Pei-Lin ^{[2
]}

Jhou, Yi-Jhen ^{[1
]}

Hou, Duen-Ren ^{[1
]}

机构：

[1] Natl Cent Univ, Dept Chem, Taoyuan 32001, Taiwan

[2] Natl Tsing Hua Univ, Instrument Ctr, Hsinchu 300044, Taiwan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 19期

关键词：

ALPHA-GLUCOSIDASE INHIBITORS; AMINOGLYCOSIDE ANTIBIOTICS; CHEMOENZYMATIC SYNTHESIS; BIOSYNTHETIC-PATHWAY; CONVENIENT SYNTHESIS; DERIVATIVES; INOSITOL; DESYMMETRIZATION; INOSAMYCIN; COMPLEX;

D O I：

10.1021/acs.joc.3c01064

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective synthesis of nabscessin C (1), an aminocyclitol amide with antimicrobial activity, is reported. Starting from myo-inositol, (+)-nabscessin C was synthesized in 12 isolation steps. Desymmetrization of 2-deoxygenated 4,6-dibenzylinositol was achieved using lipase from porcine pancreas (PPL), and the stereochemistry was established by X-ray crystallography. This method has the potential for synthesizing other cyclitol-derived compounds.

引用

收藏

页码：13528 / 13534

页数：7

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