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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.

8-epi-Salvinorin B: crystal structure and affinity at the κ opioid receptor