Ethyl Acetate → HCID 57856997, compound

Participants

Reaction Conditions

Reaction Steps

(3aR,4R,5R,6aS)-4-((R,E)-3-(Benzo[b]thiophen-2-yl)-3-(tert-butyldiphenylsilyloxy)prop-1-enyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one (7a, limiting reagent) is dissolved in anhydrous THF (0.5 M) under a nitrogen atmosphere and cooled to −78° C. A solution consisting of DIBAL-H (1 M in toluene, 2 molar equivalents) is added to the reaction mixture dropwise and stirred for 3 hours. Ethyl acetate (20 mL) is added and the mixture is stirred for an additional 5 minutes. The mixture is then treated with 30% aqueous K, Na tartrate and stirred vigorously overnight. The layers are separated and the organic phase is filtered and concentrated under reduced pressure. The crude product is purified by flash chromatography on regular silica gel eluted with hexanes-ethyl acetate to afford the title intermediate 8a.

Provenance & Evidence