Intramolecular ortho photocycloaddition of salicyclic acid derivatives: Multiple-step reaction cascades and their synthetic application

水杨酸衍生物的分子内邻位光环加成：多步级联反应及其合成应用

• 批准号: 422215986
• 负责人: Professor Dr. Thorsten Bach
• 金额: --
• 依托单位: Lehrstuhl für Organische Chemie I
• 依托单位国家: 德国
• 项目类别: Research Grants
• 财政年份: 2019
• 资助国家: 德国
• 起止时间: 2018-12-31 至 2021-12-31
• 项目状态: 已结题
• 来源: https://gepris.dfg.de/gepris/projekt/422215986?language=en
• 关键词: Intramolecular; ortho; photocycloaddition; salicyclic; acid

The project aims at the development of a photochemical reaction cascade and its application to the synthesis of terpene natural products. The cascade reaction will be studied on salicylic acid derivatives and includes in the first step an intramolecular ortho photocycloaddition to a bicyclic octadiene. In two additional steps, compounds with a bicyclo[4.2.0]octane structure are formed by thermal disrotatory ring opening and photochemical disrotatory [4pi] cyclization. In our specific case, simple and easily accessible aromatic substrates will deliver products with a complex, three-dimensional skeleton, which is found in protoilludanes. The reaction cascade will be applied to the synthesis of this class of natural products. Methodology studies, which address all issues of selectivity will serve to meet the challenges posed by the synthetic targets. An enantioselective variant of the described reaction cascade will be developed.

该项目旨在开发光化学反应级联及其在萜烯天然产品合成中的应用。级联反应将研究水杨酸衍生物，并包括在第一步的分子内邻位的二环occurring加成。在另外两个步骤中，通过热对旋开环和光化学对旋[4 pi]环化形成具有双环[4.2.0]辛烷结构的化合物。在我们的特定情况下，简单且易于获得的芳香底物将提供具有复杂三维骨架的产品，这在原伊鲁烷中发现。该反应级联将应用于这类天然产物的合成。方法学研究涉及所有选择性问题，将有助于应对合成目标带来的挑战。将开发所述反应级联的对映选择性变体。