3,3-Dimethyl-1,2,3,4-tetrahydrocyclopenta[b]indole-1,2-dione (bruceolline E)

Abstract

The title compound, C13H11NO2, crystallizes with two mol­ecules in the asymmetric unit. The crystal packing is stabilized by N—H⋯O hydrogen bonds, which link the mol­ecules into chains along [10], and weak C—H⋯O inter­actions.

Bruceolline J: 2-hydroxy-3,3-dimethyl-2,3-dihydrocyclopenta[b]indol-1(4H)-one

“…Although there has been limited attention from the synthetic community given to these compounds, a previous synthesis of bruceolline E has been reported (Jordan et al, 2011). The crystal structures of bruceolline D (Lopchuk et al, 2013) and bruceolline E (Jordon et al, 2012) have been disclosed. In view of the importance of cyclopenta[b]indole alkaloids, we report here the crystal structure of the title compound, C 13 H 13 NO 2 , (I).…”

Total Synthesis of Bruceolline I

“…Despite their potential in medicinal chemistry, only a few syntheses of these natural alkaloids, as well as an extremely limited number of biological studies on the isolated compounds, have thus far been reported. , The syntheses of bruceollines E ( 2 ) and J ( 3 ) have been reported by Gribble and co-workers, , who also published the X-ray crystallographic structure of bruceolline E . A concise stereoselective synthesis of bruceolline J ( 3 ) was reported in 2015 by Dethe and Kumar, and, more recently, the first synthesis of bruceolline H ( 5 ) was reported by us …”