HCID 86744702, compound → HCID 86744701, compound

Participants

Reaction Steps

A solution of methyl (3R,5S)-(E)-3,5-dihydroxy-7-[4-(4-fluorophenyl)-2-isopropyl-1-oxo-1,2-dihydroisoquinolin-3-yl]hept-6-enoate (as prepared in Example 10; 1.6 g) in dichloromethane (160 ml) was stirred at room temperature under argon with the exclusion of light. Manganese dioxide was added portionwise (4×4 g) over 3 hours and the mixture stirred for a further 17 hours. The mixture was filtered through diatomaceous earth and the filter pad washed with dichloromethane (3×50 ml). The combined filtrate and washings were evaporated to give a viscous orange gum which was purified by flash chromatography on silica gel using diethyl ether as eluant to give methyl (3R)-(E)-7-[4-(4-fluorophenyl)-2-isopropyl-1-oxo-1,2-dihydroisoquinolin-3-yl]-3-hydroxy-5-oxohept-6-enoate as a yellow foam (NMR (in CDCl3): 1.70 (6H, d, J=8 Hz), 2.47 (2H, d, J=6 Hz), 2.58 (2H, m), 3.30 (1H, d, J=4 Hz), 3.76 (3H, s), 4.28-4.58 (2H, m plus sept), 5.99 (1H, d, J=16 Hz), 6.97-7.59 (8H, m), 8.43 (1H, m)].

Provenance & Evidence