Formal Synthesis of (±)-Salvinorin A via Gold(I) Catalysis.
Huy Tran, Philippe McGee, Louis Barriault
Chemistry - A European Journal September 1, 2023 DOI: 10.1002/chem.202301640 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Theoretical or philosophical paper Peer reviewed |
|---|---|
| Topics | Salvia divinorum |
| Keywords | Gold Natural product Neoclerodane Terpenoids Total synthesis |
| Key points | Reports a formal synthesis of (±)-salvinorin A in which two gold(I) catalytic processes, combined with an intermolecular Diels-Alder reaction and a gold(I)-catalyzed photoredox reaction, generate the natural product framework in eight steps with high diastereoselectivity. |
Abstract
The formal synthesis of (±)-salvinorin A is presented. Our approach utilizes two distinct gold(I) catalytic processes. The combination of a gold(I)-catalyzed reaction with an intermolecular Diels-Alder reaction followed by a gold(I)-catalyzed photoredox reaction generated in eight steps the framework of the natural product with high diastereoselectivity.
Comparable studies
Other theoretical and historical papers on salvia divinorum, most cited first.
| Study | Year | Design | Participants |
|---|---|---|---|
| Total synthesis of the hallucinogenic neoclerodane diterpenoid salvinorin A. | 2008 | Theoretical or philosophical paper | |
| The claustrum's proposed role in consciousness is supported by the effect and target localization of Salvia divinorum. | 2014 | Theoretical or philosophical paper | |
| Total Synthesis of (-)-Salvinorin A. | 2016 | Theoretical or philosophical paper | |
| Scalable and modular synthesis enables pharmacological diversification of salvinorins | 2026 | Theoretical or philosophical paper | |
| Title: DMT, Salvinorin A, and Stress Regulation: An Exploratory Neuropharmacological Research Proposal | 2026 | Theoretical or philosophical paper |
Citations in the library
Cites 9
- Salvinorin A: a potent naturally occurring nonnitrogenous kappa opioid selective agonist. Proceedings of the National Academy of Sciences September 3, 2002
- Salvinorin, a new trans-neoclerodane diterpene from Salvia divinorum(Labiatae) Journal of the Chemical Society Perkin Transactions 1 1982
- Salvinorin A: from natural product to human therapeutics. Molecular interventions October 1, 2006
- Total synthesis of the hallucinogenic neoclerodane diterpenoid salvinorin A. Organic Letters April 3, 2008
- Total Synthesis of (-)-Salvinorin A. Chemistry - A European Journal December 12, 2016
and 4 more in the library