Acetic Acid → (3aR,4R,5R,6aS)-4-((R)-3-Hydroxy-5-phenylpentyl)hexahydro-2H-cyclopenta[b]furan-2,5-diol

Participants

Reaction Conditions

Reaction Steps

A mixture of compound [11a] (0.55 g), acetic acid (2 ml), THF (2 mL) and water (2 mL) was stirred at 40-50° C. for 4 hours (TLC monitoring). The mixture was basified with 1 N aq. potassium hydroxide to pH 10-11 and the product was extracted with dichloromethane (3×20 mL). The combined organic layers were dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (elution with gradient ethyl acetate/hexane from 1:2 to 3:1 v/v) to give 0.18 g (43%) of the compound [11b] as a colorless oil. 1H NMR (CD3OD) is compatible with literature data.

Provenance & Evidence