A potentially divergent and rapid route to analogues of deoxycyclitols, pentopyranoses, 6-deoxyhexoses, and hexoses.
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.
Audouard
Christophe
C
Department of Chemistry, University of Leicester, University Road, Leicester LE1 7RH, UK.
Fawcett
John
J
Griffith
Gerry A
GA
Kérourédan
Erwan
E
Miah
Afjal
A
Percy
Jonathan M
JM
Yang
Hongli
H