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

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...

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Bibliographic Details
Published in:Journal of organic chemistry 2018-09, Vol.83 (17), p.10573-10579
Main Authors: Modugu, Nagi Reddy, Mehta, Goverdhan
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b01389