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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Total Syntheses of (-)-Conidiogenone B, (-)-Conidiogenone, and (-)-Conidiogenol
Bo Xu1, Wen Xun1, Shaobin Su1
1The 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.
Abstract:
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.
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