Biomimetic Assembly of Leucoridine A1. Issue 9 (17th February 2015)

• Record Type: Journal Article
• Authors: Benayad, Sarah; Beniddir, Mehdi A.; Evanno, Laurent; Poupon, Erwan
• Is Part Of: European journal of organic chemistry. Issue 9(2015)
• Page Start: 1894
• Page End: 1898
• Publication Date: 2015-02-17
• Subjects: Alkaloids -- Bisindole -- Leucoridine -- Biomimetic synthesis -- Rauhut–Currier­; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500041
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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. Abstract : The biomimetic cascade 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 an imino‐Rauhut–Currier reaction affords the natural ( S )‐diastereomer of leucoridine A as the sole product.