Total Synthesis of 20-Norsalvinorin A. 1. Preparation of a Key Intermediate
Ylva E. Bergman, Roger Mulder, Patrick Perlmutter
The Journal of Organic Chemistry February 20, 2009 DOI: 10.1021/jo802623n (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Peer reviewed |
|---|---|
| Topics | Salvia divinorum |
| Citations | 21 |
Abstract
The key tricyclic intermediate 3a, for the total synthesis of the C(20)-nor analogue of salvinorin A, was prepared in seven steps from 3-furaldehyde. Key steps involved a highly regio- and diastereoselective Lewis acid assisted Diels-Alder reaction followed by base-promoted epimerization and a completely stereoselective conjugate reduction.
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
- Synthesis of neoclerodane diterpenes and their pharmacological effects. Topics in current chemistry 2011
- Identification of clerodane diterpene modifying cytochrome P450 (CYP728D26) in Salvia divinorum - en route to psychotropic salvinorin A biosynthesis. Physiologia plantarum 2024
- 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 5
- Salvinorin A: a potent naturally occurring nonnitrogenous kappa opioid selective agonist. Proceedings of the National Academy of Sciences September 3, 2002
- Divinorin A, a psychotropic terpenoid, and divinorin B from the hallucinogenic Mexican mint, Salvia divinorum The Journal of Organic Chemistry November 1, 1984
- Total synthesis of the hallucinogenic neoclerodane diterpenoid salvinorin A. Organic Letters April 3, 2008
- Intramolecular Diels-Alder/Tsuji allylation assembly of the functionalized trans-decalin of salvinorin A. Organic Letters December 7, 2007
- Studies Towards the Synthesis of Salvinorin A Australian Journal of Chemistry June 13, 2006