Goniomitine: An Overview on the Chemistry of This Indole Alkaloid

Abstract

This paper reports an overview on the chemistry of the indole alkaloid goniomitine focusing, mainly, on the methods of synthesis related to this natural product and analogs.

Synthesis of N-Fused Polycyclic Indoles via Ligand-Free Palladium-Catalyzed Annulation/Acyl Migration Reaction

“…A gram-scale reaction with substrate 1o was carried out with 1 mol % of Pd­(OAc) 2 as catalyst and furnished DHPI 3o in 74% yield. Notably, Li et al also developed an efficient synthesis of 3o with rhodium catalyst and finished the formal synthesis of goniomitine. , Here, we offered a complementary synthetic route to aminal 7 including double alkylation of 3o and a one-pot anti-Markovnikov hydroamination/reductive cyclization of 6 . , More generally, this method provides access to versatile synthetic intermediates that have previously been utilized in alkaloid synthesis. Hydrazinolysis of phthalimide 3p afforded tryptamine 8 in 84% yield.…”