Synthesis of vicenin-1 and 3, 6,8- and 8,6-di-C-beta-D-(glucopyranosyl-xylopyranosyl)-4',5,7-trihydroxyflavones using two direct C-glycosylations of naringenin and phloroacetophenone with unprotected D-glucose and D-xylose in aqueous solution as the key reactions.
Vicenin-3 was synthesized from naringenin via a short five-step reaction, which included two regioselective direct C-glycosylations with d-glucose and d-xylose (yields: 22% and 30%, respectively) as the key reactions for a total yield of 4.4%. Vicenin-1 was also synthesized from phloroacetophenone via a 10-step reaction, including the same glycosylation described above, for a total yield of 2.7% with a vicenin-3 yield of 1.7%.
Sato
Shingo
S
Graduate School of Science and Engineering, Yamagata University, Yamagata, Japan. shingo-s@yz.yamagata-u.ac.jp
Koide
Tomoyuki
T
D000098:Acetophenones / Q000737:chemistry*; D047310:Apigenin / Q000138:chemical synthesis* / Q000737:chemistry; D044950:Flavanones / Q000737:chemistry*; D047309:Flavones / Q000138:chemical synthesis* / Q000737:chemistry; D005947:Glucose / Q000737:chemistry*; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D012996:Solutions; D014867:Water / Q000737:chemistry*; D014994:Xylose / Q000737:chemistry*
D000098:Acetophenones; D044950:Flavanones; D047309:Flavones; D005960:Glucosides; D012996:Solutions; C117329:vicenin; D014867:Water; D047310:Apigenin; C107067:2,4,6-trihydroxyacetophenone; D014994:Xylose; C005273:naringenin; D005947:Glucose