Biomimetic assembly of leucoridine A

Leucoridine A is a complex bis-indole alkaloid isolated in 2010 from Leuconotis griffithii (Apocynaceae) showing moderate cytotoxicity towards human KB cells (IC₅₀= 1µM) [1]. The three-step biomimetic assembly of leucoridine A is described [2]. The hemisynthetic route provides suitable conditions toward the central 3-spiro-1, 2, 3, 4-dehydropiperidine ring connecting the two subunits of this highly congested structure. The biomimetic assembly by an imino-Rauhut-Currier reaction affords the natural (S)-diastereomer of leucoridine A as the sole product. The sequence, repeated in a one-pot procedure, supports a non-enzymatic pathway for the assembly of this complex alkaloid and known related alkaloids.

Keywords: Leucoridine A, biomimetic synthesis, alkaloid.

References:

[1] Gan CY, EtOH T, Hayashi M, Komiyama K, Kam TS. Leucoridines A-D, cytotoxic Strychnos-Strychnos bisindole alkaloids from Leuconotis. J Nat Prod 2010; 73: 1107 – 1111

[2] Benayad S, Beniddir MA, Evanno L, Poupon E. Biomimetic assembly of Leucoridine A. Eur J Org Chem 2015; 1894 – 1898

No conflict of interest has been declared by the author(s).