Hydrogen Peroxide → (z)-7-((1r,2s,3r)-3-Hydroxy-2-{3-[hydroxy-(1-propyl-cyclobutyl)-methyl]-phenyl}-5-oxo-cyclopentyl)-hept-5-enoic acid ethyl amide

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

Representative procedure for reduction of the C9 ketone: (Z)-7-((1R,2S,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-{4-[(tert-butyl-dimethyl-silanyloxy)-cyclohexyl-methyl]-phenyl}-5-hydroxy-cyclopentyl)-hept-5-enoic acid methyl ester (6-1). L-selectride (300 μL, 0.3 mmol, 1 M/THF) was added to a −78° C. solution of ketone 5-3 (159 mg, 0.24 mmol) in 12 mL THF. The reaction was stirred for 30 min. at −78° C. and then 3% H2O2 (7 mL) was added. The reaction was stirred for 2 h at room temperature and then was poured into saturated NH4Cl solution. The mixture was extracted with ethyl acetate (3×50 mL) and the combined ethyl acetate solution was washed with brine and then was dried (Na2SO4), filtered and evaporated. Purification by flash chromatography on silica gel (8% ethyl acetate/hexanes) gave the title alcohol (149 mg, 93%).

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