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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 18
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Original Articles

Synthesis and Cytotoxicity of 9‐Substituted Benzo[de]chromene‐7,8‐dione and 5‐Benzyl‐9‐substituted Benzo[de]chromene‐7,8‐dione

, , , , , , , , , & show all
Pages 2667-2684 | Received 24 Feb 2006, Published online: 16 Feb 2007
 

Abstract

New Mansonone analogues of 9‐substitued benzo[de]chromene‐7,8‐dione 5be and 5‐benzyl‐9‐substitued benzo[de]chromene‐7,8‐dione 6ae were prepared through a modified route. The first step involved a bulky base t‐butylamine mediated regioselective deacetylation of 2‐substituted‐1,4‐naphth‐diyl diacetate, resulting in obtaining of monoacetate 4‐acetate 2 in high yield. The mechanism of cyclization, debenzylation, and oxidation for the formation of 5ae and 6ae were discussed. The cytotoxicity of the prepared compounds 5 and 6 were comparable with naturally occurring Mansonone F.

Acknowledgments

We are indebted to the National Nature Science Foundation of China (20472117), the Guangzhou City Science Foundation, the Guangdong Provincial Science Foundation, the Scientific Research Foundation for the Returned Overseas Chinese Scholars, and the Hong Kong Polytechnic University Area of Strategic Development Fund for financial support of this study.

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