State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming, 650201, China.
Org Lett. 2014 Nov 7;16(21):5612-5. doi: 10.1021/ol502679v. Epub 2014 Oct 9.
The collective total synthesis of tetracyclic diquinane Lycopodium alkaloids, (+)-paniculatine, (-)-magellanine, (+)-magellaninone, and two analogues (-)-13-epi-paniculatine and (+)-3-hydroxyl-13-dehydro-paniculatine, has been accomplished. By logic-guided addition of a strategically useful hydroxyl group at C-3 of paniculatine, the formidable tetracyclic core was rapidly synthesized utilizing a site-specific and stereoselective aldol cyclization, thus making the ABD → ABCD tetracyclic approach to diquinane Lycopodium alkaloids attainable for the first time.
四环二蒎烷石松生物碱（+）-paniculatine、（-）-magellanine、（+）-magellaninone 及其两种类似物（-）-13-epi-paniculatine 和（+）-3-羟基-13-去氢-paniculatine 的全合成已经完成。通过在 paniculatine 的 C-3 位逻辑引导加入一个策略上有用的羟基，利用一个特定位置和立体选择性的羟醛环化反应，迅速合成了四环核心，从而首次实现了 ABD → ABCD 四环方法合成二蒎烷石松生物碱。
