Palladium-catalyzed transformations of salvinorin A, a neoclerodane diterpene from Salvia divinorum.
Andrew P Riley, Victor W Day, Hernan Navarro, Thomas E Prisinzano
Organic Letters December 6, 2013 DOI: 10.1021/ol4027528 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Peer reviewed |
|---|---|
| Interventions | Salvinorin A bromination Sonogashira coupling |
| Topics | Salvia divinorum |
| Key points | The authors report that selective bromination of salvinorin A followed by Suzuki-Miyaura and Sonogashira couplings can modify the furan ring in moderate to good yields without hydrolyzing the labile C-2 acetate or altering the stereochemistry of epimerizable centers, offering a route to furan-modified natural products for biological probe synthesis. |
Abstract
Transformations that selectively modify the furan ring present in a variety of naturals products would be useful in the synthesis of biological probes but remain largely underexplored. The neoclerodane diterpene salvinorin A, isolated from Salvia divinorum, is an example of a furan-containing natural product. Following selective bromination of salvinorin A, Suzuki-Miyaura and Sonogashira couplings were accomplished in moderate to good yields without hydrolyzing the labile C-2 acetate or altering the stereochemistry of the epimerizable centers.
Citations in the library
Cited by 3
- Synthesis and κ-opioid receptor activity of furan-substituted salvinorin A analogues. Journal of Medicinal Chemistry December 26, 2014
- The Kappa Opioid Receptor Agonist 16-Bromo Salvinorin A Has Anti-Cocaine Effects without Significant Effects on Locomotion, Food Reward, Learning and Memory, or Anxiety and Depressive-like Behaviors. Molecules June 19, 2023
- A Review of Salvinorin Analogs and their Kappa-Opioid Receptor Activity Bioorganic & Medicinal Chemistry Letters March 12, 2018
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