The State Key Laboratory of Chemical Oncogenomics, Guangdong Provincial Key Laboratory of Nano-Micro Materials Research, School of Chemical Biology and Biotechnology, Shenzhen Graduate School of Peking University, Shenzhen, 518055, China.
Institute of Marine Biomedicine, Shenzhen Polytechnic, Shenzhen, 518055, China.
Angew Chem Int Ed Engl. 2020 Sep 14;59(38):16475-16479. doi: 10.1002/anie.202007247. Epub 2020 Jul 10.
Cyclopianes are novel diterpenes featuring a highly strained 6/5/5/5 tetracyclic core embedded with 6-8 consecutive stereocenters. The concise total syntheses of (-)-conidiogenone B, (-)-conidiogenone, and (-)-conidiogenol have been accomplished in 14-17 steps. The present work features a HAT-mediated alkene-nitrile cyclization to access the cis-biquinane, a Nicholas/Pauson-Khand reaction to construct the linear triquinane, and a Danheiser annulation to afford the congested angular triquinane skeleton.
环扁柏烷类化合物是一类新型二萜类化合物，具有高度应变的 6/5/5/5 四环核心，其中嵌入有 6-8 个连续的立体中心。（-）-厚垣菌素 B、（-）-厚垣菌素和（-）-厚垣醇的简洁全合成已通过 14-17 步完成。本工作的特点是通过 HAT 介导的烯腈环化反应来获得顺式双环壬烷，通过 Nicholas/Pauson-Khand 反应来构建线性三环壬烷，以及通过 Danheiser 环合反应来提供拥挤的角型三环壬烷骨架。
