The total synthesis of illisimonin

该项目的目的是完成伊利西莫宁的全合成，伊利西莫宁是一种具有高含氧碳骨架的新萜类化合物。这种天然产品的另一个挑战是反式降冰片主链。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，伊利西莫宁的合成及其上述挑战和新特征将是这一努力的例证。它计划通过光化学[2+2]-环加成反应，然后通过钐介导的1，2-乙烯基位移动来完成合成。反式降冰片主链应借助片呐醇重排来构建。这一步骤正式导致了Norbornane主干的桥梁互换。合成的终点应该是CH2-基团在自由基条件下的后期官能化。或者，这一目标可以通过半频拿醇重排来实现。

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.