[CH3:1][CH2:2][CH2:3][C:4]1[C:9]([OH:10])=[C:8]([C:11]([CH3:13])=[O:12])[CH:7]=[CH:6][C:5]=1[OH:14].[N+](C(OCC)=O)(C(OCC)=O)=[N-].[CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][C:28]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:11]([C:8]1[CH:7]=[CH:6][C:5]([O:14][CH:32]2[CH2:31][CH2:30][CH2:29][CH:28]=[CH:27]2)=[C:4]([CH2:3][CH2:2][CH3:1])[C:9]=1[OH:10])(=[O:12])[CH3:13]To a mixture of 2,4-dihydroxy-3-propylacetophenone, 40 g, diethyl diazodicarboxylate, 51 g, and cyclohexen-2-ol, 20 g, in tetrahydrofuran, 1.5 L, cooled at 0° C., was added slowly a solution of triphenylphosphine, 80 g, in THF, 0.5 L. The mixture was stirred at room temperature for 18 hours. The volatiles were removed in vacuo. The residue was dissolved in a minimum amount of CH2Cl2 and placed on a silica gel column. Elution with 1% EtOAc/hexane yielded 20 g of the title compound as an oil. NMR (ppm) (CDCl3): 12.75 (1H, s, phenolic OH), 7.60 (1H, d, J-9 Hz, H ortho to acetyl), 6.53 (1H, d, J-9 Hz, H meta to acetyl), 5.90 (2H, m, olefinic proton), 4.87 (1H, m, CHOAc), 2.60 (3H, s, CH3).
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