Biomimetic approach to perophoramidine and communesin via an intramolecular cyclopropanation reaction.
[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.
Yang
Jun
J
Department of Chemistry of Medicinal Natural Products, West China School of Pharmacy, Sichuan University, Chengdu, PRC.
Song
Hao
H
Xiao
Xue
X
Wang
Jue
J
Qin
Yong
Y