Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, Liaoning, China.
Molecules. 2014 Jan 20;19(1):1238-49. doi: 10.3390/molecules19011238.
The elemene-type terpenoids, which possess various biological activities, contain a syn- or anti-1,2-dialkenylcyclohexane framework. An efficient synthetic route to the syn- and anti-1,2-dialkenylcyclohexane core and its application in the synthesis of (±)-geijerone and its diastereomer is reported. Construction of the syn- and anti-1,2-dialkenyl moiety was achieved via Ireland-Claisen rearrangement of the (E)-allylic ester, and the cyclohexanone moiety was derived from the iodoaldehyde via intramolecular Barbier reaction. The synthetic strategy allows rapid access to various epimers and analogues of elemene-type products.
烯丙型萜类化合物具有多种生物活性，含有顺式或反式 1,2-二烯基环己烷骨架。本文报道了一种高效合成顺式和反式 1,2-二烯基环己烷核心的方法，并将其应用于（±）-吉杰酮及其非对映异构体的合成。顺式和反式 1,2-二烯基部分的构建是通过（E）-烯丙基酯的爱尔兰-克莱森重排实现的，环己酮部分是通过碘代醛的分子内巴尔比耶反应得到的。该合成策略可以快速获得各种环氧型产物的差向异构体和类似物。
