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

ABSTRACT: Novel semisynthetic analogs of salvinorin A, a full agonist having extraordinary affinity as well as selectivity for the ?-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 (?-opioid receptor).

SUBMITTER: Bikbulatov RV

PROVIDER: S-EPMC2344139 | biostudies-literature | 2008 Feb

REPOSITORIES: biostudies-literature

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

Bikbulatov Ruslan V RV Stewart Jeremy J Jin Wentao W Yan Feng F Roth Bryan L BL Ferreira Daneel D Zjawiony Jordan K JK

Tetrahedron letters 20080201 6

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 ...[more]

PMID: 19197341

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