Tributylphosphine → HCID 131717030, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (3R,4R)3-t.butyldimethylsilyloxy-4-methoxy-4-methyl-l-tributylstannyl-l-octene 2 (0.58 g, 1 mmol) in THF (1 ml) was treated at -78° C. under nitrogen with n-butyllithium (0.65 ml, 1.6 M in hexane), stirred for 10 min at -78° C. and a solution of copper (I) iodide (0.19 g, 1 mmol) and tri-n-butyl phosphine (0.65 ml, 2.6 mmol) in 1 ml of THF was added. The reaction mixture was warmed to -40° C. and stirred for 1 h when a solution of the (3R)3-t.butyldimethylsilyloxy-5-oxo-l-cyclopenteneheptanoic acid, methyl ester (0.35 g, 1 mmol) in THF (1 ml) was added. The mixture was stirred at -40° C. for 1 h before acetic acid (0.1 ml) was added. The mixture was allowed to warm to room temperature, diluted with 100 ml of hexane, washed with water, NaHCO3 saturated, and brine and then dried over MgSO4. Solvents were flash-evaporated (20 Torr, 30° C.) and the oily residue purified by chromatography on silica gel 25 g, 230-400 mesh, eluant: petroleum ether (100 ml), then petroleum ether/EtOAc: 95/5 (200 ml), then petroleum ether/EtOAc: 92/8. The product containing fractions were combined and solvents removed in vacuo to afford 0.13 g of pure (8R,11R,12R,15R,16R)-11,15-di-t.butyldimethylsilyloxy-16-methoxy-9-oxo-prost-13-en-1-oic acid, methyl ester.

Provenance & Evidence