The total synthesis of illisimonin

本项目的目的是完成具有高含氧碳骨架的新萜类化合物--伊里斯莫宁的全合成。这种天然产品的另一个挑战是输血的曲马多烷主链。 本项目的目的是为完成复杂天然产物的合成提供新的概念和方法，而具有上述挑战性和新特征的Illisimonin的合成应该是这一奋进的一个展示案例。计划使用光化学[2+2]-环加成，然后通过钐介导的乙烯基位置的1，2-移位来完成合成。反式稠合的双烷骨架应借助于频哪醇重排来构建。这一步骤正式导致交换的桥梁的十六烷骨干。合成的最终游戏应该是在自由基条件下CH 2-基团的后期官能化。或者，该目标可以通过半频哪醇重排来实现。

The aim of this project is to complete the total synthesis of illisimonin, a new terpenoid with a highly oxygenated carbon skeleton. An additional challenge in this natural product is the trans-fused norbornane backbone. The aim of this project is to provide new concepts and methods for completing the synthesis of complex natural products and the synthesis of illisimonin with its above-mentioned challenges and new feature should be a show case of this endeavor. It is planned to complete the synthesis using a photochemical [2+2]-cycloaddition followed by a samarium-mediated 1,2-shift of the vinylic position. The trans-fused norbornane backbone should be constructed with the aid of a pinacol rearrangement. This step leads formally to an exchange of the bridges of the norbornane backbone. The end game of the synthesis should be the late-stage functionalization of a CH2-group under radical conditions. Alternatively, this goal can be achieved through a semi-pinacol rearrangement.