Institute of Chemical Biology, Henan University, Kaifeng, Henan 475004, P.R. China.
Mini Rev Med Chem. 2013 May 1;13(6):845-53. doi: 10.2174/1389557511313060007.
The γ-butenolide structural motif is a prominent feature in many bioactive natural products and drugs. This short review summarizes catalytic asymmetric synthesis of γ-butenolides through direct vinylogous reactions by metal complexes and organocatalysts. In light of building chiral γ-tertiary and quaternary carbon centers of butenolides, three synthetic strategies are included: 1) the reactions with furanone derivatives as nucleophiles, 2) olefination of γ,γ- disubstituted butenolides and 3) the reactions by using γ,γ-disubstituted butenolides as nucleophiles.
γ-丁内酯结构基序是许多生物活性天然产物和药物的突出特征。本综述总结了通过金属配合物和有机催化剂的直接 vinylogous 反应催化不对称合成 γ-丁内酯。鉴于构建手性γ-叔碳和季碳中心的丁内酯,包括三种合成策略:1)作为亲核试剂的呋喃酮衍生物的反应,2)γ,γ-二取代丁内酯的烯化反应和 3)使用γ,γ-二取代丁内酯作为亲核试剂的反应。