A Potentially Divergent and Rapid Route to Analogues of Deoxycyclitols, Pentopyranoses, 6-Deoxyhexoses, and Hexoses
2004; American Chemical Society; Volume: 6; Issue: 23 Linguagem: Inglês
10.1021/ol0482902
ISSN1523-7060
AutoresChristophe Audouard, John Fawcett, Gerry A. Griffith, E. Kerouredan, Afjal H. Miah, Jonathan M. Percy, Hongli Yang,
Tópico(s)Marine Sponges and Natural Products
ResumoDirect 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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