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

Abstract

The 12-membered cyclo­penta­[b]indole ring system in the title compound, C13H13NO2, deviates only slightly from planarity (r.m.s. deviation = 0.051 Å). In the crystal, N—H⋯O and O—H⋯O hydrogen bonds link the mol­ecules into sheets parallel to (100). The five-membered cyclopentanone ring is in slightly distorted envelope conformation with the C atom bearing the hydroxy substituent as the flap.

A Short, Protecting Group-Free Total Synthesis of Bruceollines D, E, and J

“…A variety of reductants worked well including sodium borohydride, borane-dimethyl sulfide, and catecholborane. The structure was confirmed by X-ray crystallography …”