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 κ opioid receptors.
|Number of pages||5|
|Journal||Bioorganic and Medicinal Chemistry Letters|
|State||Published - Jun 15 2006|
Bibliographical noteFunding Information:
This work was supported by National Institutes of Health, National Institute on Drug Abuse Grant DA18151 (to TEP), and in part by the Intramural Research Program of the NIH, NIDA. The authors also thank Vic Parcell and Lynn Teesch of the High Resolution Mass Spectrometry Facility, University of Iowa, for mass spectral analysis.
- Salvia divinorum
- Salvinorin A
ASJC Scopus subject areas
- Molecular Medicine
- Molecular Biology
- Pharmaceutical Science
- Drug Discovery
- Clinical Biochemistry
- Organic Chemistry