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

Author: Huang Shi   Luo Yi   Huang Zhi   Wang Xing   Bu Xian   Liu Pei   Ma Lin   Xie Bing   Liu Zong   Li Yue   Chan Albert  

Publisher: Taylor & Francis Ltd

ISSN: 0039-7911

Source: Synthetic Communications, Vol.36, Iss.18, 2006-09, pp. : 2667-2684

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Abstract

New Mansonone analogues of 9‐substitued benzo[ de ]chromene‐7,8‐dione 5b – e and 5‐benzyl‐9‐substitued benzo[ de ]chromene‐7,8‐dione 6a – e 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 5a – e and 6a – e were discussed. The cytotoxicity of the prepared compounds 5 and 6 were comparable with naturally occurring Mansonone F.

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