Total synthesis of the hallucinogenic neoclerodane diterpenoid salvinorin A.
Masato Nozawa, Yuhki Suka, Takashi Hoshi, Toshio Suzuki, Hisahiro Hagiwara
Organic Letters April 3, 2008 DOI: 10.1021/ol800101v (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Theoretical or philosophical paper Peer reviewed |
|---|---|
| Topics | Salvia divinorum |
| Keywords | Chemical synthesis Hallucinogens |
| Citations | 63 |
| Key points | Describes a 20-step total synthesis of salvinorin A from an enantiomerically pure hydroxy-Wieland-Miescher ketone. |
Abstract
Total synthesis of salvinorin A (1), a neoclerodane diterpenoid having the most potent hallucinogenic activity and a selective kappa-opioid agonist, was completed in 20 steps starting from enantiomerically pure hydroxy-Wieland-Miescher ketone 5.
Comparable studies
Other theoretical and historical papers on salvia divinorum, most cited first.
| Study | Year | Design | Participants |
|---|---|---|---|
| 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 | |
| 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 27
- Neuropharmacology of the naturally occurring kappa-opioid hallucinogen salvinorin A. Pharmacological Reviews June 1, 2011
- Biosynthesis of the psychotropic plant diterpene salvinorin A: Discovery and characterization of the Salvia divinorum clerodienyl diphosphate synthase The Plant Journal November 19, 2016
- Total Synthesis of (-)-Salvinorin A. Chemistry - A European Journal December 12, 2016
- DARK Classics in Chemical Neuroscience: Salvinorin A. ACS Chemical Neuroscience December 2, 2020
- Neoclerodanes as atypical opioid receptor ligands. Journal of Medicinal Chemistry May 9, 2013
and 22 more in the library
Cites 13
- Divinorin A, a psychotropic terpenoid, and divinorin B from the hallucinogenic Mexican mint, Salvia divinorum The Journal of Organic Chemistry November 1, 1984
- Salvinorin C, a new neoclerodane diterpene from a bioactive fraction of the hallucinogenic Mexican mint Salvia divinorum. Organic Letters November 29, 2001
- Neo-clerodane diterpenes from the hallucinogenic sage Salvia divinorum. Journal of Natural Products December 1, 2006
- Biosynthesis of salvinorin A proceeds via the deoxyxylulose phosphate pathway. Phytochemistry July 1, 2007
- Intramolecular Diels-Alder/Tsuji allylation assembly of the functionalized trans-decalin of salvinorin A. Organic Letters December 7, 2007
and 8 more in the library