5-Cyclopentyl-5-hydroxy-9-(4-hydroxy-2,5-dimethyl-phenyl)-3-oxo-non-8-ynoic Acid Methyl Ester → 6-Cyclopentyl-6-[4-(2-methylsulfanyl-phenyl)-but-3-ynyl]-dihydro-pyran-2,4-dione

Participants

Reaction Steps

The desired product was prepared analogously to example F(1), substituting 5-cyclopentyl-5-hydroxy-9-(2-methylsulfanyl-phenyl)-3-oxo-non-8-ynoic acid methyl ester (43 mg, 0.11 mmol) from Step 2 below in place of 5-cyclopentyl-5-hydroxy-9-(4-hydroxy-2,5-dimethyl-phenyl)-3-oxo-non-8-ynoic acid methyl ester. Yield: 38 mg, 97%. 1H NMR (CDCl3) δ: 1.41-1.69 (m, 8H), 1.94-2.01 (m, 2H), 2.13-2.18 (m, 1H), 2.36 (s, 3H), 2.55 (t, J=7.45 Hz, 2H), 2.67 (d, J=16.17 Hz, 1H), 2.87 (d, J=16.17 Hz, 1H), 3.34 (d, J=8.84 Hz, 2H), 6.93-7.01 (m, 2H), 7.14-7.16 (m, 1H), 7.24 (d, J=6.32 Hz, 1H). MS (ESI): 355 (M−H).

Provenance & Evidence