Acetic Acid → 1,2-Dihydroxy-3-allyloxy-6-[(Z)-2-(3,4,5-trimethoxyphenyl)vinyl]-benzene

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Reaction Steps

Tetrabutylammonium fluoride (0.24 mL, 0.24 mmol, 1M in THF) was added to a solution of 1,2-di(t-butyldimethylsilyloxy)-3-allyloxy-6-[(Z)-2-(3,4,5-trimethoxyphenyl)vinyl]-benzene (69 mg, 0.120 mmol) and glacial acetic acid (14 μL, 0.24 mmol) in THF 4 mL at 0° C. The reaction mixture was allowed to warm to rt overnight, then cooled to 0° C. and water was added. The reaction mixture was extracted with t-BuOMe (3×) and the organic phase was dried (Na2SO4) and evaporated to dryness. Purification by column chromatography (SiO2 3:7 EtOAc:cyclohexane) gave ZSB-84 (36 mg, 84%) as an 96:4 mixture of Z:E isomers:

Provenance & Evidence