Studies Towards the Synthesis of Salvinorin A
Anthony R. Lingham, Helmut M. Hügel, Trevor J. Rook
Australian Journal of Chemistry June 13, 2006 DOI: 10.1071/ch05338 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Peer reviewed |
|---|---|
| Topics | Salvia divinorum |
| Key points | The authors report synthetic routes toward the ketone and lactone rings of salvinorin A. A Diels–Alder reaction of a non-racemic 3-furylamine with methyl acrylate in aqueous media, followed by selective ether bridge cleavage, gave a cyclohexenone with preserved stereochemistry at C2. A separate model route to the lactone ring used one-pot deconjugation/esterification of 2-bromocrotonyl chloride with a furyl alcohol, then Reformatsky-mediated ring closure. |
Abstract
Salvinorin A 1, a psychoactive neoclerodane diterpenoid from the Mexican sage S. divinorum, has gained interest as a selective ?-opioid receptor agonist. Non-racemic 3-furylamines 9a and 9b have been prepared from (+)-pseudoephedrine and (–)-ephedrine for application in the stereoselective synthesis of the ketone ring of 1. Diels–Alder reaction of 9b with methyl acrylate in aqueous media, followed by selective ether bridge cleavage, has allowed access to the cyclohexenone 17 with preservation of stereochemistry at C2. A model route to the lactone ring has also been achieved through a one-pot deconjugation/esterification procedure of 2-bromocrotonyl chloride 20 to the furyl alcohol 19 followed by Reformatski-mediated ring closure.
Citations in the library
Cited by 12
- Neuropharmacology of the naturally occurring kappa-opioid hallucinogen salvinorin A. Pharmacological Reviews June 1, 2011
- Total Synthesis of the Neoclerodane Diterpene Salvinorin A via an Intramolecular Diels–Alder Strategy Organic Letters May 22, 2018
- Total Synthesis of 20-Norsalvinorin A. 1. Preparation of a Key Intermediate The Journal of Organic Chemistry February 20, 2009
- Synthesis of neoclerodane diterpenes and their pharmacological effects. Topics in current chemistry 2011
- Highly Oxygenated Diterpenoids Associated to the Central Nervous System: Syntheses of Salvinorin and Forskolin Journal of Synthetic Organic Chemistry Japan 2009
and 7 more in the library
Cites 15
- 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
- Divinorin A, a psychotropic terpenoid, and divinorin B from the hallucinogenic Mexican mint, Salvia divinorum The Journal of Organic Chemistry November 1, 1984
- Salvia divinorum and the unique diterpene hallucinogen, Salvinorin (divinorin) A. Journal of Psychoactive Drugs 1994
- Salvinorin C, a new neoclerodane diterpene from a bioactive fraction of the hallucinogenic Mexican mint Salvia divinorum. Organic Letters November 29, 2001
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