A potentially divergent and rapid route to analogues of deoxycyclitols, pentopyranoses, 6-deoxyhexoses, and hexoses |
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Authors: | Audouard Christophe Fawcett John Griffith Gerry A Kérourédan Erwan Miah Afjal Percy Jonathan M Yang Hongli |
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Affiliation: | Department of Chemistry, University of Leicester, University Road, Leicester LE1 7RH, UK. |
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Abstract: | Direct precursors to analogues of pentopyranoses, 6-deoxyhexoses, and hexoses, in which a CF(2) center replaces the pyranose oxygen, have been synthesized rapidly from trifluoroethanol. A simple scaleable allylation reaction delivers ethers which undergo dehydrofluorination/metalation, followed by addition to either acrolein or cinnamaldehyde, to afford allylic alcohols. Fluorine-assisted [3,3]-rearrangement followed by reduction with sodium borohydride delivers diols, which undergo RCM smoothly to afford cyclohexene diols. |
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