Biomimetic approach to perophoramidine and communesin via an intramolecular cyclopropanation reaction |
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Authors: | Yang Jun Song Hao Xiao Xue Wang Jue Qin Yong |
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Institution: | Department of Chemistry of Medicinal Natural Products, West China School of Pharmacy, Sichuan University, Chengdu, PRC. |
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Abstract: | reaction: see text] Starting from tryptamine 4 and isatin 5, a biomimetic approach to the pentacyclic substructure 1 of perophoramidine and communesin was developed. The key steps were to create a stable three/six bicyclic system 2 on the 2,3-double bond of an indole derivative 3 by an intramolecular cyclopropanation, followed by ring opening of the resulting cyclopropane ring with the in situ generated amine group of an aniline. |
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