Glenn W Goetchius

Autoxidation of salvinorin A under basic conditions.

The Journal of Organic Chemistry November 1, 2005 Thomas A Munro, Glenn W Goetchius, Bryan L. Roth et al.

[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...