Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry , Sichuan University, Chengdu 610064 , People's Republic of China.
Org Lett. 2018 Apr 6;20(7):1945-1948. doi: 10.1021/acs.orglett.8b00479. Epub 2018 Mar 19.
A flexible strategy has been developed to synthesize divergent flavonoids bearing a chiral A-ring. As two key steps, the coupling via a boron-mediated aldol condensation and the cyclization via a highly stereoselective intramolecular Michael addition of 1,3-diketone proceed under mild conditions; thus, the chiral flavonoids bearing C-7 oxy functional groups or olefinic bonds are both easily accessible. Using this approach, the first synthesis of (+)-cryptogione F, (+)-cryptocaryanone B, and (+)-cryptochinones A and C, as well as stereoselective synthesis of (+)-cryptocaryone and (+)-cryptocaryanone A, were achieved from 2-deoxy-d-ribose in high overall yields.
一种灵活的策略已被开发出来，用于合成具有手性 A 环的发散黄酮类化合物。作为两个关键步骤，通过硼介导的醛缩合偶联和通过 1,3-二酮的高立体选择性分子内迈克尔加成进行的环化在温和条件下进行；因此，易于获得具有 C-7 氧官能团或烯键的手性黄酮类化合物。使用这种方法，从 2-脱氧-d-核糖以高总收率实现了 (+)-隐酮 F、（+）-隐卡酮 B 和（+）-隐醌 A 和 C 的首次合成，以及（+）-隐卡酮和（+）-隐卡酮 A 的立体选择性合成。
