The structure of brevicolline

Synthesis of Enantiomerically Pure (−)-(S)-Brevicolline

“…The β-carboline alkaloid brevicolline ( 1 ), the major alkaloid of the plant Carex brevicollis DC (Cyperacee), belongs to a group of pharmacologically interesting compounds and was isolated, , determined, and chemically modified 30 years ago. Since that time, syntheses of racemic 1 were carried out, for example, by Winterfeldt or Leete, both using tryptamine as starting compound.…”

“…The reported effects of these compounds include antineoplastic (tubuline binding), [2][3][4] anticonvulsive, hypnotic and anxiolytic (benzodiazepine receptor inhibitoric), 2,5-8 antiviral, 9 antimicrobial, 3 and topoisomerase II inhibition 10 and inhibition of cGMP-dependent processes. 11 The β-carboline alkaloid brevicolline (1), the major alkaloid of the plant Carex brevicollis DC (Cyperacee), belongs to a group of pharmacologically interesting compounds 12 and was isolated, 13,14 determined, 15 and chemically modified 16 30 years ago. Since that time, syntheses of racemic 1 were carried out, for example, by Winterfeldt 17 or Leete, 18 both using tryptamine as starting compound.…”