Department of Chemistry, National Dong Hwa University, Hualien, 97401, Taiwan, ROC.
Org Biomol Chem. 2011 Nov 7;9(21):7306-8. doi: 10.1039/c1ob06383a. Epub 2011 Sep 14.
An isomer-divergent synthesis of naturally occurring pericosines A and B is described starting from a known D-ribose derived ene-diol in 35% and 41% overall yields respectively of which the latter is the best synthetic method reported for pericosine B. The key features of this synthesis include the stereoselective NHK vinylation of the terminal aldehyde to the versatile diolefinic chiral intermediate and elegant conversions of the same to the corresponding final products via RCM (Ring Closing Metathesis).
本文描述了一种从已知的 D-核糖衍生的烯二醇出发，分别以 35%和 41%的总收率立体选择性地合成天然存在的培可辛 A 和 B 的异构体发散合成方法，其中后者是报道的培可辛 B 的最佳合成方法。该合成的关键特点包括末端醛的立体选择性 NHK 乙烯化作用，得到多功能二烯烃手性中间体，以及通过 RCM（环封闭复分解）将相同的中间体转化为相应的最终产物的巧妙转化。
