Intramolecular Diels-Alder/Tsuji allylation assembly of the functionalized trans-decalin of salvinorin A.
Aaron C Burns, Craig J Forsyth
Organic Letters December 7, 2007 DOI: 10.1021/ol7024058 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Theoretical or philosophical paper Peer reviewed |
|---|---|
| Topics | Salvia divinorum |
| Keywords | Diterpenes, clerodane Naphthalenes Molecular structure Stereoisomerism |
| Key points | Reports an enantioselective synthesis of the highly functionalized trans-decalin core of salvinorin A, in which a tetraene intermediate made in six steps from an L-(+)-tartaric acid derivative undergoes an intramolecular Diels-Alder/Tsuji allylation sequence to set three contiguous stereocenters, two of them quaternary. |
Abstract
An enantioselective synthesis of the highly functionalized trans-decalin core (2) of salvinorin A is described. The tetraene 4 was synthesized in six steps from a known L-(+)-tartaric acid derivative. Three contiguous stereocenters, two of them quaternary, on the trans-decalin were established asymmetrically by an intramolecular Diels-Alder/Tsuji allylation sequence.
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 | |
| 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 | |
| Salvia divinorum induces body awareness changes comparable to metamorphic symptoms in the Alice in Wonderland syndrome | 2019 | Theoretical or philosophical paper |
Citations in the library
Cited by 10
- Neuropharmacology of the naturally occurring kappa-opioid hallucinogen salvinorin A. Pharmacological Reviews June 1, 2011
- 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
- DARK Classics in Chemical Neuroscience: Salvinorin A. ACS Chemical Neuroscience December 2, 2020
- Total Synthesis of 20-Norsalvinorin A. 1. Preparation of a Key Intermediate The Journal of Organic Chemistry February 20, 2009
and 5 more in the library