Chiral synthesis of sesterterpene YW3699 bearing inhibitory activity of GPI synthesis and its absolute configuration

本研究的目的是合成对疟原虫GPI合成具有抑制活性的手性化合物YW 3699，确定其绝对构型，为活性检测提供物质基础，并寻找活性与结构的关系。合成了许多模型化合物，并尝试通过调节底物中存在的官能团来环化为8元碳环的复分解反应以高产率产生所需化合物。产物的立体化学由NMR光谱确定。以手性形式制备具有与天然产物非常相似的官能团的底物。

The purpose of this study is to synthesize chiral compound of YW3699, which exhibits inhibitory activity against GPI synthesis of malaria tipanosoma, to determine the absolute configuration and to provide the substance to test the activity as well as to find a relationship between activity and structures. Many model compounds were synthesized and metathesis reactions to cyclize to 8-membered carbocycles were attempted to yield the desired compounds in high yield by tuning the functional groups present in the substrates. The stereochemistry of the products were determined by NMR spectroscopy. The substrate bearing the functional groups quite similar to the natural product was prepared in chiral forms.