Total Syntheses of (−)-Conidiogenone B, (−)-Conidiogenone,and (−)-Conidiogenol |
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| Authors: | Dr Bo Xu Dr Wen Xun Shaobin Su Prof Dr Hongbin Zhai |
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| Institution: | 1. 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;2. 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
These authors contributed equally to this work. |
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| 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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| Keywords: | cyclopianes Danheiser annulation diterpenes Nicholas/Pauson––Khand reaction total synthesis |
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