Short synthesis of a novel class of salvinorin A analogs with hemiacetalic structure

Ruslan V Bikbulatov; Jeremy Stewart; Wentao Jin; Feng Yan; Bryan L Roth; Daneel Ferreira; Jordan K Zjawiony

doi:10.1016/j.tetlet.2007.12.041

Short synthesis of a novel class of salvinorin A analogs with hemiacetalic structure

Tetrahedron Lett. 2008 Feb 4;49(6):937-940. doi: 10.1016/j.tetlet.2007.12.041.

Authors

Ruslan V Bikbulatov¹, Jeremy Stewart, Wentao Jin, Feng Yan, Bryan L Roth, Daneel Ferreira, Jordan K Zjawiony

Affiliation

¹ Department of Phamacognosy, School of Pharmacy, University of Mississippi, University, MS 38677-1848, USA.

Abstract

Novel semisynthetic analogs of salvinorin A, a full agonist having extraordinary affinity as well as selectivity for the κ-opioid receptor (KOR), were obtained in good yields. The derivatives are remarkable for their unusual and unique hemiacetal structure in the salvinorin series of compounds. The formation of the hemiacetal occurs with epimerization at C-12, thus preserving the original configuration of salvinorin A. The dimethyl ester derivative of the hemiacetal was found to have an affinity for both KOR and MOR (μ-opioid receptor).

Abstract

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