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

Tetrahedron Letters

Volumn 49, Issue 6, 2008, Pages 937-940

  Bikbulatov, Ruslan V ^a   Stewart, Jeremy ^a   Jin, Wentao ^a   Yan, Feng ^b   Roth, Bryan L ^b   Ferreira, Daneel ^a,c   Zjawiony, Jordan K ^a,c  

^a UNIVERSITY OF MISSISSIPPI   (United States)

^b UNIVERSITY OF NORTH CAROLINA SCHOOL OF MEDICINE   (United States)

^c UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

Dual affinity; Hemiacetal; KOR ligands; Salvinorin A

Indexed keywords

KAPPA OPIATE RECEPTOR; MU OPIATE RECEPTOR; SALVINORIN A;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; EPIMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 38049050761     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.12.041     Document Type: Article

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26. 2 (0.13 mmol) in benzene (1 mL) was added at room temperature to a stirred solution of hemiacetal 2 (20 mg, 0.05 mmol) in methanol (5 mL). The mixture was stirred at room temperature for 30 min and concentrated to give the corresponding dimethyl ester 9. The product was purified by column chromatography using a short silica column and hexanes/ethyl acetate (2:1). Yield was 18.3 mg (87%).
27. 4). Removal of the solvent under reduced pressure afforded acetate (10), which was purified by column chromatography using a short silica column and hexanes/ethyl acetate (2:1). Yield was 8.9 mg (73%).
28. 2 (2 mL) was stirred at room temperature for 3 h. Removal of the solvent under reduced pressure afforded hydroxyketone (11), which was purified by column chromatography using a short silica column and hexanes/ethyl acetate (3:2). Yield was 8.1 mg (81%).