A Flexible and Divergent Strategy to Flavonoids with a Chiral A-Ring Featuring Intramolecular Michael Addition: Stereoselective Synthesis of (+)-Cryptocaryone, (+)-Cryptogione F, and (+)-Cryptocaryanones A and B, as Well as (+)-Cryptochinones A and C

作者：Liu, Xiaojing; Jia, Junhao; Jia, Yuanliang; Gu, He; Luo, Jingwen; Chen, Xiaochuan^*

来源：Organic Letters, 2018, 20(7): 1945-1948.

DOI：10.1021/acs.orglett.8b00479

• MEDIATED ALDOL REACTIONS
• CRYPTOCARYA-CHINENSIS
• CYTOTOXIC FLAVONOIDS
• KETONES
• SEGMENT
• ESTERS
• LEAVES

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-o-ribose in high overall yields.

• 出版日期2018-4-6
• 单位四川大学