Abstract: A concise synthesis procedure for the total synthesis of natural product(±)-Aiphanol 12, a novel stilbenolignan having a stilbene-phenylpropane unit with a dioxane moiety, was achieved by using simple aldehydes as the starting materials. The key steps were oxidative coupling of coniferyl alcohol 4 with catechol 6 using Ag₂O as the catalyst to give the 1,4-benzodioxane intermediate 7, followed by a selective protection of the phenolic hydroxy group of 7 to afford 8, which was oxidized by NaIO₄/OsO₄(cat.) to give the key intermediate aldehyde 9. Then after Wittig-Horner reaction followed by conversion of Z-isomer to E-isomer using thiophenol in refluxing benzene in the presence of azoisobutyronitrile(AIBN) to produce 11, which underwent deprotection with diluted HCl in methanol to afford the titled compound(±)-Aiphanol 12 conveniently.

Key words: ?(±)-Aiphanol, Stilbene, 1,4-Benzodioxane, Ag₂O coupling reaction, NaIO₄/OsO₄(cat.) oxidation