Departamento de Química, División de Ciencias Naturales y Exactas , Universidad de Guanajuato , Campus Guanajuato, Cerro de la Venada S/N , 36040 Guanajuato , México.
Departamento de Farmacia, División de Ciencias Naturales y Exactas , Universidad de Guanajuato , Campus Guanajuato, Noria Alta S/N , 36050 Guanajuato , México.
J Org Chem. 2018 Sep 7;83(17):10627-10635. doi: 10.1021/acs.joc.8b01436. Epub 2018 Aug 22.
The modular protecting-group-free total synthesis of 3-methylkealiiquinone, an analogue of the marine alkaloid kealiiquinone, was accomplished in seven steps. A regioselectively constructed functionalized arylbenzimidazolone moiety and dimethyl squarate were used as the only two building blocks. A thermal ring expansion via 6π-conrotatory ring closure to build the quinone fragment gave rise to the desired linear analogue of the natural compound along with a nondescribed structurally attractive angular naphtho[1,2- d]imidazole regioisomer. The IC values for the compounds were determined on three cancer cell lines.
3-甲基凯阿内酯，一种海洋生物碱凯阿内酯的类似物，采用无保护基模块合成法，经 7 步反应完成全合成。通过区域选择性构建的功能化芳基苯并咪唑酮片段和二甲基丙二腈作为仅有的两个构建块。通过热环扩张经 6π-协同环闭合构建醌片段，得到了天然化合物的所需线性类似物，以及一个结构上有吸引力的非描述性角萘[1,2-d]咪唑并区域异构体。化合物的 IC 值在三种癌细胞系上进行了测定。
