8-epi-Salvinorin B: crystal structure and affinity at the κ opioid receptor
There have been many reports of epimerization of salvinorins at C-8 under basic conditions, but little evidence has been presented to establish the structure of these compounds. We report here the first crystal structure of an 8-epi-salvinorin or derivative: the title compound, 2b. The lactone adopt...
| Main Authors: | , , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2007-01-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Online Access: | https://doi.org/10.1186/1860-5397-3-1 |
| Summary: | There have been many reports of epimerization of salvinorins at C-8 under basic conditions, but little evidence has been presented to establish the structure of these compounds. We report here the first crystal structure of an 8-epi-salvinorin or derivative: the title compound, 2b. The lactone adopts a boat conformation with the furan equatorial. Several lines of evidence suggest that epimerization proceeds via enolization of the lactone rather than a previously proposed indirect mechanism. Consistent with the general trend in related compounds, the title compound showed lower affinity at the kappa opioid receptor than the natural epimer salvinorin B (2a). The related 8-epi-acid 4b showed no affinity. |
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| ISSN: | 1860-5397 |