Autoxidation of salvinorin A under basic conditions.
Thomas A Munro, Glenn W Goetchius, Bryan L. Roth, Timothy A Vortherms, Mark A Rizzacasa
The Journal of Organic Chemistry November 1, 2005 DOI: 10.1021/jo051813e (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Theoretical or philosophical paper Peer reviewed |
|---|---|
| Topics | Salvia divinorum |
| Keywords | Hydroxides Potassium compounds Methanol Diterpenes, clerodane Molecular conformation Oxidation-reduction Stereoisomerism |
| Key points | Treatment of salvinorin A with KOH in methanol gives enedione 3 (previously proposed as dienone 7) and, after methylation, secotriesters 4a-c, with a mechanism proposed for the autoxidations. Compound 4a showed weak kappa-opioid receptor affinity, whereas divinatorins A-C showed none. Reduction of 3 to a salvinorin diol failed, but deacetylation of salvinorin C offered a route to it, and a TLC method for identifying salvinorin 8-epimers is presented. |
Abstract
[reaction: see text] Treatment of salvinorin A (1a) with KOH in MeOH gave the enedione 3, for which the dienone structure 7 was recently proposed. Also isolated, after methylation, were the secotriesters 4a-c. A mechanism for this unusual series of autoxidations is proposed. Surprisingly, 4a showed weak affinity at the kappa-opioid receptor. Divinatorins A-C (2a-c) showed no affinity at opioid receptors. Attempted reduction of 3 to a novel salvinorin diol (9d) was unsuccessful, but careful deacetylation of salvinorin C (9a) provided a viable route to this compound. A general method for identifying salvinorin 8-epimers by TLC is also presented.
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 | |
| Title: DMT, Salvinorin A, and Stress Regulation: An Exploratory Neuropharmacological Research Proposal | 2026 | Theoretical or philosophical paper | |
| Salvia Divinorum: entrSalvia divinorum: Entre la prohibición y la construcción de su conocimientoe a proibição e a construção do seu saber | 2022 | Theoretical or philosophical paper |
Citations in the library
Cited by 12
- Neuropharmacology of the naturally occurring kappa-opioid hallucinogen salvinorin A. Pharmacological Reviews June 1, 2011
- Salvia divinorum and salvinorin A: an update on pharmacology and analytical methodology. Planta Medica August 1, 2007
- Neo-clerodane diterpenes from the hallucinogenic sage Salvia divinorum. Journal of Natural Products December 1, 2006
- Neoclerodanes as atypical opioid receptor ligands. Journal of Medicinal Chemistry May 9, 2013
- Synthesis of neoclerodane diterpenes and their pharmacological effects. Topics in current chemistry 2011
and 7 more in the library
Cites 13
- Salvinorin A: a potent naturally occurring nonnitrogenous kappa opioid selective agonist. Proceedings of the National Academy of Sciences September 3, 2002
- Salvinorin A, an active component of the hallucinogenic sage salvia divinorum is a highly efficacious kappa-opioid receptor agonist: structural and functional considerations. Journal of Pharmacology and Experimental Therapeutics March 1, 2004
- Identification of the molecular mechanisms by which the diterpenoid salvinorin A binds to kappa-opioid receptors. Biochemistry June 21, 2005
- Salvinorin C, a new neoclerodane diterpene from a bioactive fraction of the hallucinogenic Mexican mint Salvia divinorum. Organic Letters November 29, 2001
- A facile method for the preparation of deuterium labeled salvinorin A: synthesis of [2,2,2-2H3]-salvinorin A. Bioorganic & Medicinal Chemistry Letters October 18, 2004
and 8 more in the library