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Total Synthesis of (-)-Daphenylline

DOI: 10.1002/anie.201902268  full text link

文献汇报人:李慧

汇报日期: 20191130

图文摘要:

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  • 推荐原因:

虎皮楠生物碱( Daphniphyllum alkaloids )是一大类从虎皮楠属植物中分离得到的生物碱的总称,由于复杂多变的骨架特征,其吸引了大量合成研究小组的兴趣。邱发洋课题组以(S)-Carvone作为手性源,通过设计全新的合成策略,以19步(分离纯化步骤)及7.6%的总产率实现了(-)-Daphenylline的不对称全合成。该全合成路线使手性得到极好的控制并成为目前该分子的全合成中反应步骤最少、产率最高的路线。此外,部分中间体可通过扩环合成虎皮楠生物碱家族的其他骨架。该研究成果的亮点在于以价廉易得的天然手性源(S)-Carvone为起始原料,运用简单的合成砌块,以极好的立体选择性,简洁、高效地实现了(-)-Daphenylline的全合成。关键步骤包括Mg(ClO4)2催化的酰胺环化, Diels-Alder 环加成反应,Robinson环化/芳构化,Friedel-Crafts环化。


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