Efficient Construction of Chiral Spiro[benzo[g]chromene-oxindole] Derivatives via Organocatalytic Asymmetric Cascade Cyclization

Feng-Feng Pan; Wei Yu; Zheng-Hang Qi; Chunhua Qiao; Xing-Wang Wang

doi:10.1055/s-0033-1341061

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(09): 1143-1156
DOI: 10.1055/s-0033-1341061

feature article

Efficient Construction of Chiral Spiro[benzo[g]chromene-oxindole] Derivatives via Organocatalytic Asymmetric Cascade Cyclization

Feng-Feng Pan

^aKey Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. of China Fax: +86(512)65880378 eMail: wangxw@suda.edu.cn

,

Wei Yu

^bCollege of Pharmaceutical Science, Soochow University, Suzhou 215123, P. R. of China Fax: +86(512)65882092 eMail: qiaochunhua@suda.edu.cn

,

Zheng-Hang Qi

^aKey Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. of China Fax: +86(512)65880378 eMail: wangxw@suda.edu.cn

,

Chunhua Qiao*

^bCollege of Pharmaceutical Science, Soochow University, Suzhou 215123, P. R. of China Fax: +86(512)65882092 eMail: qiaochunhua@suda.edu.cn

,

Xing-Wang Wang*

^aKey Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. of China Fax: +86(512)65880378 eMail: wangxw@suda.edu.cn

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Abstract

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Abstract

Pyranonaphthoquinone units are common in molecular structures with significant biological and pharmaceutical activities. Herein, the organocatalytic asymmetric cascade Michael cyclization reaction of 2-hydroxynaphthalene-1,4-diones to isatylidene malononitriles has been developed, which provided the desired spiro[4H-benzo[g]chromene-indoline] derivatives in up to 99% yield with up to 99% ee. To illustrate the potential utility of these products, a further transformation was conducted to give a spiropolyheterocyclic compound in moderate yield without loss of enantioselectivity (>99% ee). Biological evaluation of these spiro[benzo[g]chromene-indoline] derivatives has revealed excellent antiproliferative activity against a number of cancer cell lines, with a high inhibition rate ranging from 93% to 99% at a concentration of 50 μM.

Key words

cascade cyclization - isatylidene malononitriles - hydroxynaphthalenes - spirobenzo[g]chromenes - spirooxindoles

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Zusatzmaterial

Supporting Information