HCID 57857071, compound → HCID 57857010, compound

Participants

Reaction Conditions

Reaction Steps

(Z)-Methyl 7-((1R,2R,5S)-2-((R,E)-3-(benzo[b]thiophen-2-yl)-3-(tert-butyldiphenylsilyloxy)prop-1-enyl)-3-methylene-5-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enoate (17a, limiting reagent) is dissolved in a 3:1 methanol and 1 N LiOH solution (0.01 M) and stirred at 4° C. Upon completion of the reaction, as judged by TLC, the reaction mixture is diluted with ethyl acetate, washed with 5% aqueous KHSO4 and brine. The organic phase is dried over sodium sulfate, filtered, and the solvent is evaporated. The crude product is purified by flash chromatography on regular silica gel eluted with hexanes-ethyl acetate to afford the title intermediate 19a.

Provenance & Evidence