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Yang, J. et al.

Biomimetic Approach to Perophoramidine and Communesin via an Intramolecular Cyclopropanation Reaction.

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.[1]

References

Biomimetic Approach to Perophoramidine and Communesin via an Intramolecular Cyclopropanation Reaction. Yang, J., Song, H., Xiao, X., Wang, J., Qin, Y. Org. Lett. (2006) [Pubmed]

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