Methanol → HCID 22810245, compound

Participants

Reaction Steps

At -40°, 230 mg. of sodium borohydride is added in incremental portions to a solution of 470 mg. of (1S,5R,6R,7R,3S)-7-acetoxy-6-[(1E)-7-methyl-3-oxo-1,6-octadienyl]-3-(4-methoxycarbonyl-1-butyl)-2-oxabicyclo[3,3,0]octane in 14 ml. of methanol and 4 ml. of THF. The mixture is stirred for 1 hour at -40° and then combined with 0.6 ml. of glacial acetic acid, concentrated under vacuum, combined with methylene chloride, the organic extract shaken in 4% sodium bicarbonate solution, washed neutral with water, dried over magnesium sulfate, and evaporated under vacuum. After separation by chromatography on silica gel, ether/pentane (1+1) yields 120 mg. of the corresponding β-configured compound and 160 mg. of the title compound as a colorless oil.

Provenance & Evidence