Synthetic Communications p. 2667 - 2684 (2006)
Update date:2022-08-03
Topics:
Huang, Shi-Liang
Luo, Yi
Huang, Zhi-Shu
Wang, Xing-Yuan
Bu, Xian-Zhang
Liu, Pei-Qing
Ma, Lin
Xie, Bing-Fen
Liu, Zong-Chao
Li, Yue-Ming
Chan, Albert S. C.
Gu, Lian-Quan
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. Copyright Taylor & Francis Group, LLC.
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Doi:10.1039/b612597b
(2006)Doi:10.1002/lipi.19630651017
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(2011)Doi:10.1021/jo01078a005
(1960)Doi:10.1021/jo01134a002
(1953)Doi:10.1055/s-2006-950246
(2006)