The synthesis of β-carba-xylo and arabino pyranosides of cholestanol is described. The synthetic strategy, which is analogous to the Postema approach to C-glycosides, centers on the ring closing metathesis of an enol ether-alkene precursor to give a cyclic enol ether that is elaborated to a carba-pyranoside via hydroboration-oxidation on the olefin. The method, which is attractive for its modularity and stereoselectivity, may find wider applications to carba-hexopyranosides and other complex cycloalkyl ether frameworks.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5137374 | PMC |
| http://dx.doi.org/10.1016/j.carres.2016.03.002 | DOI Listing |
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