Novel total syntheses of (±)-oxerine by intramolecular Heck reaction |
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| Authors: | Jingrui Zhao Xiaoxia YangXueshun Jia Shengjun LuoHongbin Zhai |
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| Affiliation: | a Laboratory of Modern Synthetic Organic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
b Department of Chemistry, Shanghai University, Shanghai 200436, China |
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| Abstract: | Both a three-step and a five-step syntheses of monoterpene alkaloid (±)-oxerine from alcohol 6 have been accomplished. In the second approach, the synthetic efficiency was enhanced by implementing a one-pot protocol (deprotonation/silylation/ alkylation/desilylation). The construction of the cyclopenta[c]pyridine framework was realized by an intramolecular Heck reaction, which should be adaptable for the synthesis of other related monoterpene pyridine alkaloids. |
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| Keywords: | intramolecular Heck reaction monoterpene oxerine pyridine alkaloid syntheses |
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