Common-intermediate strategy for synthesis of conduritols and inositols via beta-hydroxy cyclohexenylsilanes.
[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.
Heo
Jung-Nyoung
JN
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.
Holson
Edward B
EB
Roush
William R
WR
D003500:Cyclization; D003511:Cyclohexanols / Q000138:chemical synthesis*; D053138:Cyclohexenes; D007202:Indicators and Reagents; D007294:Inositol / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D003511:Cyclohexanols; D053138:Cyclohexenes; D007202:Indicators and Reagents; C090988:conduritol B; D007294:Inositol