Sato Shingo, Akiya Toshiki, Nishizawa Hiroaki, Suzuki Toshiyuki
Department of Chemistry and Chemical Engineering, Faculty of Engineering, Yamagata University, 4-3-16 Jonan, Yonezawa-shi, Yamagata 992-8510, Japan.
Carbohydr Res. 2006 Jun 12;341(8):964-70. doi: 10.1016/j.carres.2006.02.019. Epub 2006 Mar 20.
Three naturally occurring di-C-glycosylflavonoids, phloretin (dihydrochalcone), naringenin (flavanone), and apigenin (flavone) bis-6,8-C-beta-D-glucopyranosides (4, 5, and 6), were synthesized in total yields of 52.3%, 53.5%, and 36.4%, respectively, starting from the key compound, di-C-beta-D-glucopyranosylphloroacetophenone (1). Benzyl protection of the phenolic hydroxyls in 1 and a subsequent aldol condensation with benzyloxybenzaldehyde led to the production of chalcone 3, which, after hydrogenolysis or acid hydrolysis and deprotection, gave 4 and 5, respectively. The acetylation of 5, followed by DDQ oxidation and deprotection, gave 6.
三种天然存在的二 - C - 糖基黄酮类化合物，根皮素（二氢查耳酮）、柚皮素（黄烷酮）和芹菜素（黄酮）双 - 6,8 - C - β - D - 吡喃葡萄糖苷（4、5和6），分别以52.3%、53.5%和36.4%的总收率合成，起始原料为关键化合物二 - C - β - D - 吡喃葡萄糖基间苯三酚（1）。1中酚羟基的苄基保护以及随后与苄氧基苯甲醛的羟醛缩合反应生成查耳酮3，其经过氢解或酸水解及脱保护反应后，分别得到4和5。5经乙酰化反应，随后进行DDQ氧化和脱保护反应，得到6。
