Enantioselective Formal Synthesis of the Cytotoxic Topoisomerase II Inhibitor Deoxythysanone, Catalyzed by Chiral Spiroborate Ester

被引：2

作者：

Chopade, M. U. ^{[1
,2
]}

Nikalje, M. D. ^{[2
]}

Patil, H. S. ^{[3
]}

Chopade, A. U. ^{[4
]}

机构：

[1] St Dnyaneshwar Mahavidyalaya, Dept Chem, Aurangabad 431120, Maharashtra, India

[2] Savitribai Phule Univ, Dept Chem, Pune 411007, Maharashtra, India

[3] Moreshwar Coll, Dept Chem, Bhokardan 431114, India

[4] Dahiwadi Coll, Dahiwadi 415508, India

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 56卷 / 04期

关键词：

homobenzylic ketone; spiroborate esters; asymmetric reduction; alcohol; deoxythysanone; 3C-PROTEASE INHIBITOR; PYRANONAPHTHOQUINONE ANTIBIOTICS; DEOXY ANALOGS; STEREOCHEMISTRY; ELEUTHERIN; REDUCTION; THYSANONE;

D O I：

10.1134/S1070428020040181

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bioactive pyranonaphthoquinone analogs, (1R,3S)-deoxythysanone, (1R,3S)-thysanone, and (1R,3S)-demethoxythysanone can be efficiently synthesized from a common intermediate product, (S)-3-methyl-3,4-dihydro-1H-isochromene-5,8-dione. We have developed a short synthetic route to pyranonaphthoquinone antibiotics, which involves enantioselective reduction of homobenzylic ketone in the presence of a chiral spiroborate catalyst with 87% enantiomeric excess as the key step. The subsequent oxa-Pectet-Spengler reaction, followed by oxidative demethylation, afforded deoxythysanone.

引用

页码：693 / 697

页数：5

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