消旋藁本酚及其类似物的合成研究

STUDIES ON THE SYNTHESIS OF dl LIGUSTIPHENOL AND ITS ANALOGUES

藁本酚是从中药藁本根茎中分离到的新的倍半萜类化合物，有较强的免疫抑制、抗炎活性。为了进一步研究该化合物的药理活性，对其进行了合成研究。以异丁醛、间甲酚为起始原料，经溴取代、芳烃碘代、羟基保护、格氏反应、Ａｌｄｏｌ缩合反应，脱保护等６步反应完成了消旋藁本酚的全合成。经１ＨＮＭＲ，ＭＳ，ＩＲ分析，并与天然产物藁本酚比较，目的物得到证实。为了研究藁本酚的构效关系，设计并合成了５个类似物。初步的药理研究没有发现相应的生理活性。

S (-) Ligustiphenol is a new sesquiterpene with antiinflammatory and immunosuppressive activities. In order to study its pharmacological activities, the total synthesis of its racemat was carried out by a six step reaction sequence including bromination of aldehyde, iodination of m cresol, protection of phenolic hydroxyl, Grignard reaction, Aldol condensation, etc. The target compound was characterized by comparing its 1H NMR, MS and IR spectra with natural (-) ligustiphenol. In order to study the structure activity relationships of ligustiphenol, its five analogues were designed and synthesized. The pharmacological screening of these analogues has been performed.