Biomimetic Synthesis of Macahydantoins A and B from Lepidium meyenii, and Structure Revision of Macahydantoin B as a Class of Thiohydantoin with a 4-Methyl-hexahydropyrrolo[1,2-c] imidazole Skeleton

文献类型： 外文期刊

第一作者： Zhou, Min

作者： Zhou, Min;Ma, Hang-Ying;Xing, Huan-Huan;Li, Ping;Li, Gan-Peng;Geng, Hui-Chun;Hu, Qiu-Fen;Zhou, Min;Ma, Hang-Ying;Xing, Huan-Huan;Li, Ping;Li, Gan-Peng;Hu, Qiu-Fen;Geng, Hui-Chun;Yang, Guang-Yu

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期刊名称：ORGANIC LETTERS （ 影响因子：6.005； 五年影响因子：5.551 ）

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收录情况： SCI

摘要： Phytochemical investigation on Lepidium meyenii led to the discovery of macahydantoin C (3), a new thiohydantoin with a 1,3-diazabicydo[3.3.1]nonane core, the spectral properties of which indicate a potential structural misassignment of its previously reported analogue, macahydantoin B (2a). To probe this hypothesis, a concise, scalable, and biomimetic synthesis of the originally proposed 2a and its revised structure (2b) was efficiently accomplished using the modified Edman degradation as the key step from commercially available materials in 65% (three steps) and 52% (three steps) overall yields, respectively. These synthetic endeavors undoubtedly reassigned the structure of macahydantoin B as an unreported type of thiohydantoin featuring a 4-methyl-hexahydropyrrolo[1,2-c]dimidazole scaffold.

分类号： O62

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