ounds ▁may ▁be ▁reduced ▁with ▁T FA ▁and ▁tri eth yl sil ane . ▁Sub st it uted ▁fur ans ▁are ▁reduced ▁to ▁t et rah ydro fur an ▁derivatives ▁in ▁high ▁yield . ▁ ▁Est ers ▁may ▁be ▁reduced ▁to ▁alco h ols ▁under ▁conditions ▁of ▁nucle oph il ic ▁activation ▁with ▁ca es ium ▁or ▁pot ass ium ▁flu or ide . ▁ ▁Al de hy des ▁under go ▁hyd ros ily lation ▁in ▁the ▁presence ▁of ▁hyd ros il anes ▁and ▁flu or ide . ▁The ▁resulting ▁s ily l ▁eth ers ▁can ▁be ▁hydro ly zed ▁with ▁ 1 ▁M ▁hydro ch lor ic ▁acid . ▁Opt imal ▁yields ▁of ▁the ▁hyd ros ily lation ▁are ▁obtained ▁when ▁the ▁reaction ▁is ▁carried ▁out ▁in ▁very ▁polar ▁sol vent s . ▁ ▁Ac et als , ▁k et als , ▁and ▁am inals ▁are ▁reduced ▁in ▁the ▁presence ▁of ▁hyd ros il anes ▁and ▁acid . ▁Site - select ive ▁reduction ▁of ▁ac et als ▁and ▁k et als ▁whose ▁o xy gens ▁are ▁in equ ivalent ▁have ▁been ▁reported — the ▁example ▁below ▁is ▁used ▁in ▁a ▁synth esis ▁of ▁Tam if lu . ▁ ▁Other ▁functional ▁groups ▁that ▁have ▁been ▁reduced ▁with ▁hyd ros il anes ▁include ▁am ides , ▁α , β - uns atur ated ▁am ides , ▁and ▁α , β - uns atur ated ▁est ers ▁en am ines , ▁im ines , ▁and ▁az ides . ▁ ▁App lications ▁A ▁synth esis ▁of