Synthesis of asymmetrically substituted scyllo-inositol
2016
Rodriguez, Jacob | Walczak, Maciej A.
scyllo-Inositol, a rare member of the inositol family, is present in axinelloside A, a marine metabolite with interesting inhibitory activity against human telomerase. Here, we present a concise synthesis of asymmetrically substituted scyllo-inositol starting from inexpensive d-glucose. Our synthetic approach capitalizes on Ferrier rearrangement of vinyl acetate and stereoselective reduction of the resultant ketone to establish the scyllo-inositol core. The protocol provides access to large quantities of scyllo-inositol in 10 steps from commercially available materials.
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