Beilstein J. Org. Chem.2021,17, 730–736, doi:10.3762/bjoc.17.62
, Yokohama University of Pharmacy, 601 Matano, Totsuka-ku, Yokohama 245-0066, Japan 10.3762/bjoc.17.62 Abstract The first total synthesis of the pyrrolo[2,3-c]quinoline alkaloid trigonoineB (1) was accomplished via a six-step sequence involving the construction of an N-substituted 4-aminopyrrolo[2,3-c
]quinoline framework via electrocyclization of 2-(pyrrol-3-yl)benzene containing a carbodiimide moiety as a 2-azahexatriene system. The employed six-step sequence afforded trigonoineB (1) in 9.2% overall yield. The described route could be employed for the preparation of various N-substituted 4
-aminopyrroloquinolines with various biological activities.
Keywords: 2-azahexatiriene system; carbodiimide; electrocyclization; pyrrolo[2,3-c]quinoline; trigonoineB; Introduction
In 2011, two novel alkaloids, namely trigonoine A and B, were isolated from the leaves of Trigonostemon lii by Hao and co-workers [1]. The
PDF
Graphical Abstract
Figure 1:
Natural products possessing the pyrrolo[2,3-c]quinoline skeleton.