Department of Chemistry and Center for Cancer Research, Purdue University, West Lafayette, Indiana 47907, United States.
J Am Chem Soc. 2020 Aug 12;142(32):13677-13682. doi: 10.1021/jacs.0c06179. Epub 2020 Jul 27.
A novel palladium-catalyzed ring opening carbonylative lactonization of readily available hydroxycyclopropanols was developed to efficiently synthesize tetrahydrofuran (THF) or tetrahydropyran (THP)-fused bicyclic γ-lactones, two privileged scaffolds often found in natural products. The reaction features mild reaction conditions, good functional group tolerability, and scalability. Its application was demonstrated in a short total synthesis of (±)-paeonilide. The fused bicyclic γ-lactone products can be easily diversified to other medicinally important scaffolds, which further broadens the application of this new carbonylation method.
发展了一种新型钯催化的易得的羟基环丙醇的开环羰基环化内酯化反应，以高效合成四氢呋喃（THF）或四氢吡喃（THP）稠合双环γ-内酯，这两种稠合双环骨架通常存在于天然产物中。该反应具有温和的反应条件、良好的官能团耐受性和可扩展性。其应用在（±）-丹皮酚的简短全合成中得到了证明。稠合双环γ-内酯产物可以很容易地转化为其他具有重要药用价值的骨架，进一步拓宽了这种新的羰基化方法的应用。
