A new and stereospecific synthesis for DL-proto-quercitol has beeR dev
eloped starting from commercial 1,4-cyclohexadiene. Photooxygenation o
f 1 resulted in the formation of 3 whose configuration has been determ
ined from spectroscopic data and by chemical interconversions. LiAlH4
or thiourea reduction of the peroxide linkages in 3 gave cyclohexenetr
iol 4a. KMnO4 oxidation of the corresponding cyclohexene acetate 4b fo
llowed by ammonolysis gave 6a as the sole product in high yield.