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Concise syntheses of (+)-austrodoral and (+)-austrodoric acid Based on H2O2 mediated oxidative ring contraction |
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| Authors: | Hongbo Wei Hongli Zhang Shoule Han Shan Mu Ke Huang Guzhou Chen Weiqing Xie |
| Institution: | 1. Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, 22 Xinong Road, Yangling 712100, Shaanxi, China;2. State Key Laboratory of Stress Biology for Arid Areas, Northwest A&F University, Yangling, Shaanxi, China;3. The College of Plant Protection, Northwest A&F University, China;4. Key Laboratory of Botanical Pesticide R&D in Shaanxi Province, Yangling, Shaanxi 712100, China |
| Abstract: | Asymmetric synthesis of the marine nor-sesquiterpenoid (+)-austrodoric acid and (+)-austrodoral in seven and nine steps respectively from Wieland-Miescher ketone was described herein. The synthesis featured an oxidative ring contraction of α-formyl cyclic ketone mediated by H2O2 to forge the hydrindane scaffold together with the contiguous quaternary carbon centers simultaneously. |
| Keywords: | Corresponding author at: Shaanxi Key Laboratory of Natural Products & Chemical Biology College of Chemistry & Pharmacy Northwest A&F University 22 Xinong Road Yangling 712100 Shaanxi China Sesquiterpene Sustrodorane Asymmetric synthesis Oxidative ring contraction |
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