title: The first total synthesis of apigenin 7-O-β-D-cellobiosyl-4'-O-β-D-glucopyranoside isolated from Salvia uliginosa.
abstract: The first total synthesis of apigenin 7-O-β-D-cellobioside (5) and apigenin 7-O-β-D-cellobiosyl-4'-O-β-D-glucopyranoside (8), which were isolated from petals of Salvia patens and Salvia uliginosa, were achieved in four and six steps and 76% and 57%, respectively, overall yield, from naringenin (1). The total synthesis contained two-glycosylation, acetylation, oxidation, selective deacetylation and deprotection steps. Although this route contained six steps, the targeted compounds were obtained with higher yields and easier purifications than other synthetic methods.
authors.affiliation: Faculty of Art and Sciences, Department of Chemistry, Sakarya University, Sakarya, Turkey.
authors.forename: Fatih
authors.initials: F
authors.lastname: Sonmez
authors.forename: Mehmet
authors.initials: M
authors.lastname: Nebioglu
authors.forename: Senol
authors.initials: S
authors.lastname: Besoluk
authors.forename: Mustafa
authors.initials: M
authors.lastname: Arslan
authors.forename: Mustafa
authors.initials: M
authors.lastname: Zengin
authors.forename: Mustafa
authors.initials: M
authors.lastname: Kucukislamoglu
mesh_terms: D000107:Acetylation; D047310:Apigenin / Q000737:chemistry*; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry*; D006031:Glycosylation; D027544:Salvia / Q000737:chemistry*
chemical_list: D005960:Glucosides; D047310:Apigenin