1312614-06-4Relevant articles and documents
Towards total synthesis of communesins and perophoramidine: Unexpected cascade reaction of Michael-Mannich-Mannich additions
Wu, Haoxing,Xiao, Xue,Qin, Yong
, p. 907 - 910 (2011/06/17)
A new type of chiral amidinobenzodiene 5 was prepared from isatin in ten steps. While attempting to prepare the core structure from 5 and tryptamine derivative 17 via a hetero Diels-Alder reaction for the total synthesis of communesin and perophoramidine, we observed an unexpected three-step, one-pot cascade reaction of Michael-Manich-Manich additions. The cascade reaction between 5 and 17 yielded diasteromers 21a and 21b with a complex polycyclic skeleton of 2,3,4,5-diindolinohexahydropyrrole in 76% yield and a ratio of 3:1. The stereochemistry of 21a was confirmed by X-ray crystal-structural analysis. Georg Thieme Verlag Stuttgart · New York.