HCID 67000377, compound → HCID 57857063, compound

Participants

Reaction Steps

A mixture consisting of (3aR,4R,5R,6aS)-4-((R,E)-3-(benzo[b]thiophen-2-yl)-3-(tert-butyldiphenylsilyloxy)prop-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate (6a, limiting reagent) in methanol (0.2 M) and potassium carbonate (0.6 molar equivalent) is stirred at room temperature and the reaction progress is monitored by TLC every 30 minutes. After complete consumption of starting material, the reaction mixture is acidified with 5% aqueous KHSO4 and diluted with brine. The product is extracted with ethyl acetate twice. The combined organic layers are dried over sodium sulfate, filtered, and evaporated under reduced pressure. The crude product is purified by flash chromatography on regular silica gel eluted with hexanes-ethyl acetate (1:1) to afford the title intermediate 7a.

Provenance & Evidence