Tetrabutylammonium Fluoride → 4-Hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-6-phenyl-5,6-dihydro-pyran-2-one

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The title compound was prepared as described in General Method 7 and General Method 8 using 9.05 g (20 mmol) of 7-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-5-hydroxy-3-oxo-5-phenyl-heptanoic acid methyl ester from the previous paragraph, 40 mL (40 mmol) of 1 M tetrabutylammonium fluoride and 20 mL of THF. The resultant crude material was combined with 800 mL of 0.1N NaOH:THF (9:1). After workup the product was purified by silica gel chromatography, eluting with MeOH:CH2Cl2 (5:95 to 10:90) gave the title compound. 1H NMR (CDCl3) δ 2.24 (m, 2 H), 2.42 (m, 1H), 2.63 (m, 1 H), 2.96 (dd, 2 H), 3.33 (dd, 2 H), 5.17 (bs, 1 H), 6.73 (d, 2 H), 6.94 (d, 2 H), 7.33-7.45 (m, 5 H).

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