Facile synthesis of acacetin-7-O-β-d-galactopyranoside

Acacetin-7-O-β-d-galactopyranoside (1), a natural flavonoid isolated from flower heads of Chrysanthemum morifolium, has been reported to inhibit the replication of HIV in H9 cells. We achieved the total synthesis of compound 1 by employing a one-pot synthesis of the aglycon. The key reactions in this approach include the modified Baker–Venkataraman reaction and regio- and stereoselective O-glycosylations.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Acacetin-7-O-β-d-galactopyranoside (1), has been reported to inhibit the replication of HIV. ► Total synthesis of compound 1 employing a one-pot synthesis of aglycon. ► The key reaction in this approach includes the regio- and stereoselective O-glycosylation.