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Biomimetic Assembly of Leucoridine A
Author(s) -
Benayad Sarah,
Beniddir Mehdi A.,
Evanno Laurent,
Poupon Erwan
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500041
Subject(s) - chemistry , biomimetic synthesis , natural product , stereochemistry , diastereomer , ring (chemistry) , sequence (biology) , cascade , combinatorial chemistry , organic chemistry , biochemistry , chromatography
The three‐step biomimetic assembly of leucoridine A, a pseudosymmetric bisindole of Leuconotis griffithi (Apocynaceae) is described. The semisynthetic route provides suitable conditions toward the central 3‐spiro‐1,2,3,4‐tetrahydropiperidine ring connecting the two subunits of the highly congested structure. The biomimetic assembly by a Diels–Alder or alternatively an imino‐Rauhut–Currier reaction affords the natural ( S )‐diastereomer of leucoridine A as the sole product. The sequence, repeated in a one‐pot cascade, supports a non‐enzymatic pathway for the assembly of this bisindole and the known related alkaloids.