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American Chemical Society, Journal of Organic Chemistry, 24(70), p. 10057-10061, 2005

DOI: 10.1021/jo051813e

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Autoxidation of Salvinorin A under Basic Conditions

Journal article published in 2005 by Thomas A. Munro ORCID, Glenn W. Goetchius, Bryan L. Roth, Timothy A. Vortherms, Mark A. Rizzacasa
This paper is available in a repository.
This paper is available in a repository.

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Abstract

Treatment of salvinorin A (1a) with KOH in MeOH gave the enedione 3, for which the dienone structure 7 was recently proposed. Also isolated, after methylation, were the seco-triesters 4a—c. A mechanism for this unusual series of autoxidations is proposed. Surprisingly, 4a showed weak affinity at the κ-opioid receptor. Divinatorins A—C (2a—c) showed no affinity at opioid receptors. Attempted reduction of 3 to a novel salvinorin diol (9d) was unsuccessful, but careful deacetylation of salvinorin C (9a) provided a viable route to this compound. A general method for identifying salvinorin 8-epimers by TLC is also presented.