Methanol → HCID 22810248, compound

Participants

Reaction Steps

At -40°, 210 mg. of sodium borohydride is added in incremental portions to a solution of 390 mg. of (1S,5R,6R,7R,3S)-7-acetoxy-6-[(E)-3-oxo-1-octen-6-ynyl]-3-(4-methoxycarbonyl-1-butyl)-2-oxabicyclo[3,3,0]octane in 12 ml. of methanol and 5 ml. of tetrahydrofuran. The mixture is stirred for 1 hour at -40°, then combined with 0.5 ml. of glacial acetic acid, concentrated under vacuum, the residue mixed with methylene chloride, and the organic extract is shaken with 4% sodium bicarbonate solution and then washed neutral with water, dried over magnesium sulfate, and evaporated under vacuum. After chromatography of the residue on silica gel with ether/pentane (6+4), 110 mg. of the β-configured compound and 150 mg. of the title compound are obtained in the form of an oil.

Provenance & Evidence