Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
Org Lett. 2013 Nov 15;15(22):5846-9. doi: 10.1021/ol402906y. Epub 2013 Nov 4.
Enantioselective total syntheses of (+)-fawcettidine and (+)-lycoposerramine Q as well as the first total synthesis of (-)-lycopladine D from a common intermediate have been accomplished by a divergent path. The common intermediate was derived from a Hajos-Parrish-like diketone by a stereoselective Birch reduction and a Suzuki coupling. The synthesis of (-)-lycopladine D featured an allylic oxidation and a biomimetic aminoketalization while the route to (+)-fawcettidine and (+)-lycoposerramine Q highlighted an oxidative rearrangement.
通过发散路径，实现了 (+)-fawcettidine 和 (+)-lycoposerramine Q 的对映选择性全合成以及 (-)-lycopladine D 的首次全合成，从共同的中间体开始。共同的中间体是由立体选择性的 Birch 还原和 Suzuki 偶联反应从 Hajos-Parrish 样二酮衍生而来的。(-)-lycopladine D 的合成具有烯丙基氧化和仿生氨基缩酮化，而 (+)-fawcettidine 和 (+)-lycoposerramine Q 的路线则突出了氧化重排。
