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Autoxidation of salvinorin A under basic conditions.

ABSTRACT: [reaction: see text] 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 secotriesters 4a-c. A mechanism for this unusual series of autoxidations is proposed. Surprisingly, 4a showed weak affinity at the kappa-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.

SUBMITTER: Munro TA

PROVIDER: S-EPMC2778035 | biostudies-literature | 2005 Nov

REPOSITORIES: biostudies-literature

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Autoxidation of salvinorin A under basic conditions.

Munro Thomas A TA Goetchius Glenn W GW Roth Bryan L BL Vortherms Timothy A TA Rizzacasa Mark A MA

The Journal of organic chemistry 20051101 24

[reaction: see text] 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 secotriesters 4a-c. A mechanism for this unusual series of autoxidations is proposed. Surprisingly, 4a showed weak affinity at the kappa-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 deace ...[more]

PMID: 16292839

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