【摘要】 以醛 1和 5为起始原料 ,经几步反应后用 Ag2 O偶联 ,得到含苯并二氧六环骨架的化合物 7,化合物 7经过选择性保护酚羟基 ,再用 Na IO4 / Os O4 (cat.)氧化断裂双键 ,得到关键中间体 9,化合物 9和 1 0经过Wittig-Horner反应 ,并用苯硫酚和 AIBN实现了顺式双键向反式的转化 ,脱去保护基后完成了具有新颖结构的天然产物 (± ) -Aiphanol(1 2 )的合成 .更多还原

【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.{更多还原