A Concise Stereoselective Synthesis of Naturally Occurring d‐Xylo‐C₁₈‐Guggultetrol and its C2‐Epimer

Abstract

d-Gluconic acid δ-lactone has served as an economical and commercially available key chiral template for a concise 7-step stereoselective synthesis of d-xylo-and dlyxo-configured guggultetrols. The key steps involved are a one-pot conversion of d-gluconic acid δ-lactone to γ-vinyl-βhydroxy-γ-lactone, a chain extension through a Grignard reaction and a diastereoselective Sharpless asymmetric dihydroxylation.[a] N. . Completion of the synthesis of D-xylo-and D-lyxo-guggultetrols 1 a and 1 b and their tetraacetates.

The Potential of β‐Hydroxy‐γ‐vinyl‐γ‐lactone in the Synthesis of Natural Products and Beyond

“…Considering the vinyl bond in lactone 1 being available for dihydroxylation, we considered a concise synthesis of guggultetrols . These are C1,2,3,4‐tetrols (with C18 and C20 linear carbon atoms resembling the spingolipids) isolated from gum resin known as guggul in Ayurveda and are used for treatment of inflammation, rheumatoid arthritis, obesity, and lipid disorder .…”

“…tetrols. [44] These are C1,2,3,4-tetrols (with C18 and C20 linear carbon atoms resembling the spingolipids) isolated from gum resin known as guggul in Ayurveda and are used for treatment of inflammation, rheumatoid arthritis, obesity, and lipid disorder. [45] The naturally occurring guggultetrols have D-xylo configuration.…”