Methanol → HCID 22810233, compound

Participants

Reaction Steps

At -40°, 420 mg. of sodium borohydride is added in incremental portions to a solution of 800 mg. of (1S,5R,6R,7R,3R)-7-acetoxy-6-[(E)-3-oxo-1-octen-6-ynyl]-3-(4-methoxycarbonyl-1-butyl)-2-oxabicyclo[3,3,0]octane in 24 ml. of methanol and 10 ml. of tetrahydrofuran. The mixture is agitated for 1 hour at -40°. Then the mixture is gently combined with 1 ml. of glacial acetic acid, concentrated under vacuum, the residue combined with methylene chloride, the organic extract shaken with 4% sodium bicarbonate solution, washed neutral with water, dried with magnesium sulfate, and evaporated under vacuum. After chromatography of the residue on silica gel with ether/pentane (6+4), 250 mg. of the corresponding compound in the β-configuration is obtained, along with 266 mg. of the title compound as a colorless oil.

Provenance & Evidence