Synthesis of the Polyoxygenated Cyclohexanoid Core of Bioactive Glycosides Xylosmin and Flacourtosides E and F.

ABSTRACT

A flexible synthesis of the carbocyclic core present in glycosides xylosmin and flacourtosides E and F, natural products exhibiting antimalarial and antiarboviral activities, has been accomplished. Our approach emanates from the Diels-Alder adduct of cyclopentadiene and MOM-protected 2-hydroxymethyl- p-benzoquinone and takes advantage of the stereochemical propensity of the norbornyl-fused scaffolds to generate the dense oxy-functionalization pattern with stereocontrol, enroute to a racemic synthesis of the carbocyclic core present in the aforementioned bioactive materials. This effort augurs well for exploring chemical diversity space around their scaffold.