Synthetic studies of neoclerodane diterpenes from Salvia divinorum: selective modification of the furan ring.
Wayne W Harding, Matthew Schmidt, Kevin Tidgewell, Pavitra Kannan, Kenneth G Holden, Christina M Dersch, Richard B Rothman, Thomas E Prisinzano
Bioorganic & Medicinal Chemistry Letters June 15, 2006 DOI: 10.1016/j.bmcl.2006.03.062 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Peer reviewed |
|---|---|
| Topics | Salvia divinorum |
Abstract
A synthetic sequence has been developed to selectively functionalize the furan ring of the natural product salvinorin A (2a). The synthetic routes described convert the furan ring in 2a into an N-sulfonylpyrrole, oxazole or an oxadiazole. In addition, a procedure has been found to remove the furan skeleton completely. Biological results indicate that replacement of the furan ring with an N-sulfonylpyrrole leads to reduced affinity and efficacy at kappa opioid receptors.
Citations in the library
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- Neuropharmacology of the naturally occurring kappa-opioid hallucinogen salvinorin A. Pharmacological Reviews June 1, 2011
- Structure-based design, synthesis, and biochemical and pharmacological characterization of novel salvinorin A analogues as active state probes of the kappa-opioid receptor. Biochemistry July 28, 2009
- Salvia divinorum and salvinorin A: an update on pharmacology and analytical methodology. Planta Medica August 1, 2007
- Neo-clerodane diterpenes from the hallucinogenic sage Salvia divinorum. Journal of Natural Products December 1, 2006
- Total synthesis of the hallucinogenic neoclerodane diterpenoid salvinorin A. Organic Letters April 3, 2008
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Cites 10
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- A facile method for the preparation of deuterium labeled salvinorin A: synthesis of [2,2,2-2H3]-salvinorin A. Bioorganic & Medicinal Chemistry Letters October 18, 2004
- Synthetic studies of neoclerodane diterpenes from Salvia divinorum: semisynthesis of salvinicins A and B and other chemical transformations of salvinorin A. Journal of Natural Products 2006
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