Synthesis 2014; 46(09): 1143-1156
DOI: 10.1055/s-0033-1341061
feature article
© Georg Thieme Verlag Stuttgart · New York

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

Feng-Feng Pan
a   Key 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
b   College of Pharmaceutical Science, Soochow University, Suzhou 215123, P. R. of China   Fax: +86(512)65882092   Email: qiaochunhua@suda.edu.cn
,
Zheng-Hang Qi
a   Key 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*
b   College of Pharmaceutical Science, Soochow University, Suzhou 215123, P. R. of China   Fax: +86(512)65882092   Email: qiaochunhua@suda.edu.cn
,
Xing-Wang Wang*
a   Key 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
› Author Affiliations
Further Information

Publication History

Received: 01 February 2014

Accepted after revision: 05 March 2014

Publication Date:
10 April 2014 (online)


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.

Supporting Information

 
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