（-）-霍顿酮C的全合成。
A total synthesis of (-)-Hortonone C.
作者信息
Niroula Doleshwar, Hallada Liam P, Rogelj Snezna, Tello-Aburto Rodolfo
机构信息
Department of Chemistry, New Mexico Institute of Mining and Technology, Socorro NM 87801, United States.
Department of Chemistry, New Mexico Institute of Mining and Technology, Socorro NM 87801, United States; Department of Biology, New Mexico Institute of Mining and Technology, Socorro NM 87801, United States.
出版信息
Tetrahedron. 2017 Jan 26;73(4):359-364. doi: 10.1016/j.tet.2016.12.013. Epub 2016 Dec 11.
A total synthesis of the cytotoxic terpenoid hortonone C was accomplished and its absolute stereochemistry confirmed. Intermediate (+)- was synthesized using either an asymmetric conjugate addition strategy, or by elaboration of the Hajos-Parrish ketone. Reduction of (+)- under dissolving-metal conditions and trapping the enolate intermediate served to control the cis-stereochemistry at the ring fusion and provide a silyl enol ether necessary for ring expansion. Comparison of optical rotation data confirmed that the absolute configuration of natural hortonone C is (6,7,10).
完成了细胞毒性萜类化合物霍顿酮C的全合成，并确定了其绝对立体化学结构。中间体（+）- 通过不对称共轭加成策略或通过对哈约什-帕里什酮的衍生化来合成。在溶解金属条件下还原（+）- 并捕获烯醇盐中间体有助于控制环融合处的顺式立体化学，并提供环扩展所需的硅烯醇醚。旋光数据的比较证实天然霍顿酮C的绝对构型为（6,7,10）。
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