We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Total Synthesis and Structural Plasticity of Kratom Pseudoindoxyl Metabolites**.
- Authors
Angyal, Péter; Hegedüs, Kristóf; Mészáros, Bence Balázs; Daru, János; Dudás, Ádám; Galambos, Anna Rita; Essmat, Nariman; Al‐Khrasani, Mahmoud; Varga, Szilárd; Soós, Tibor
- Abstract
Mitragynine pseudoindoxyl, a kratom metabolite, has attracted increasing attention due to its favorable side effect profile as compared to conventional opioids. Herein, we describe the first enantioselective and scalable total synthesis of this natural product and its epimeric congener, speciogynine pseudoindoxyl. The characteristic spiro‐5‐5‐6‐tricyclic system of these alkaloids was formed through a protecting‐group‐free cascade relay process in which oxidized tryptamine and secologanin analogues were used. Furthermore, we discovered that mitragynine pseudoindoxyl acts not as a single molecular entity but as a dynamic ensemble of stereoisomers in protic environments; thus, it exhibits structural plasticity in biological systems. Accordingly, these synthetic, structural, and biological studies provide a basis for the planned design of mitragynine pseudoindoxyl analogues, which can guide the development of next‐generation analgesics.
- Subjects
KRATOM; NATURAL products; BIOLOGICAL systems; STEREOISOMERS; TRYPTAMINE; MARINE natural products; ALKALOIDS
- Publication
Angewandte Chemie, 2023, Vol 135, Issue 35, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202303700