Planta Med 2016; 82(S 01): S1-S381
DOI: 10.1055/s-0036-1596760
Abstracts
Georg Thieme Verlag KG Stuttgart · New York

Biomimetic assembly of leucoridine A

S Benayad
1   BioCIS, Univ. Paris-Sud, CNRS, LabEx LERMIT, Université Paris-Saclay, 92296 Châtenay-Malabry, France
,
MA Beniddir
1   BioCIS, Univ. Paris-Sud, CNRS, LabEx LERMIT, Université Paris-Saclay, 92296 Châtenay-Malabry, France
,
L Evanno
1   BioCIS, Univ. Paris-Sud, CNRS, LabEx LERMIT, Université Paris-Saclay, 92296 Châtenay-Malabry, France
,
E Poupon
1   BioCIS, Univ. Paris-Sud, CNRS, LabEx LERMIT, Université Paris-Saclay, 92296 Châtenay-Malabry, France
› Author Affiliations
Further Information

Publication History

Publication Date:
14 December 2016 (online)

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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.

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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