Weihai Marine Organism & Medical Technology Research Institute, Harbin Institute of Technology, Weihai 264209, P. R. China.
College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, P. R. China.
Org Biomol Chem. 2021 Nov 10;19(43):9439-9447. doi: 10.1039/d1ob01598b.
A modular strategy for meroterpenoid-type marine natural products has been developed from commercially available (+)-sclareolide using a palladium-catalyzed tandem carbene migratory insertion as one of the key steps. Its applicability is showcased by the formal synthesis of (-)-pelorol and 9--pelorol and the concise total synthesis of (+)-yahazunone and (+)-yahazunol. It is worth noting that the formal synthesis of (-)-pelorol and 9--pelorol was achieved by controlling the reaction sequence of hydrogenation and cyclization.
已开发出一种从商业可得的 (+)-喇叭茶内酯出发的,用于合成倍半萜型海洋天然产物的模块化策略,其中钯催化的卡宾迁移插入反应是关键步骤之一。其适用性通过 (-)-pelorol 和 9--pelorol 的形式合成以及 (+)-yahazunone 和 (+)-yahazunol 的简洁全合成得到了展示。值得注意的是,(-)-pelorol 和 9--pelorol 的形式合成是通过控制氢化和环化反应的顺序来实现的。