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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Common-intermediate strategy for synthesis of conduritols and inositols via beta-hydroxy cyclohexenylsilanes
Jung-Nyoung Heo1, Edward B Holson, William R Roush
1Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.
Abstract:
[reaction: see text] Syntheses of conduritols B-D and F and d-(+)-chiro- and neo-inositols from cyclohexenylsilane intermediates are described. The key cyclohexylsilane intermediates 5 and 14 were synthesized by stereoselective olefin dihydroxylation of the corresponding cyclohexenylsilanes. Selective Peterson elimination reactions and Fleming-Tamao oxidations of 5 and 14 then delivered the targeted cyclitol derivatives.
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