Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → Methyl 5-(3-((1R,2R,3R,5R)-5-chloro-2-((3S,7R,E)-3,7-dihydroxyoct-1-enyl)-3-hydroxycyclopentyl)propyl)thiophene-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

A 20 mL vial equipped with a magnetic stirbar was charged with 210 mg of THP-ether 10 (0.40 mmol) was dissolved in 6 mL of methanol. To this was then added 300 mg of pyridinium p-toluenesulfonate (1.20 mmol) and the mixture was stirred at 17° C. over 17 h. The reaction was sampled by TLC and worked up by concentration in vacuo to remove methanol. The residual products were taken up in ethyl acetate and filtered through a 10 g plug of silica gel, eluting the polar product away from the salts with ethyl acetate (300 mL). Concentration of the filtrate yielded 170 mg of products. Final preparative thin layer chromatographic purification yielded 161 mg (91%) of triol 11 as an oil; 1H NMR (CDCl3): 1.18 (d, J=6.3 Hz, 3H), 1.36-1.62 (m, 8H), 1.77 (m, 3H), 1.94 (m, 2H), 2.10-2.34 (m, 5H), 2.43 (Br s, 1H), 2.83 (m, 2H), 3.50 (br s, 1H), 3.71 (br s, 1H), 3.79 (m, 1H), 3.86 (s, 3H), 3.98 (m, 1H), 4.09 (m, 1H), 5.51 (m, 2H), 6.78 (dd, J=3.9 Hz, 1H), 7.62 (d, J=3.9 Hz, 1H).

Provenance & Evidence