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
收藏
页码：693 / 697
页数：5
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