AN EFFICIENT AND STEREOSPECIFIC SYNTHESIS OF PROTO-QUERCITOL

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.