Silyl nitronates and nitrile oxides in organic synthesis. A novel route to d,l-deoxysugars. Use of aluminum oxide as solid phase base for generation of

Novel methodology is developed for a three step synthesis of deoxyaldoses and deoxyketoses: 1. Regioselective addition of silyl nitronate or nitrile oxide to a diene. 2. Stereospecific hydroxylation of the double bond. 3. Unmasking of the aldol moiety by catalytic reduction of the 2-isoxazoline. The syntheses of D,L-deoxyribose, D,L-oleose, D,L-digitoxose, D,L-2-deoxygalactose, 1,3-dideoxyfructose, 3-deoxyfructose etc. are described. Basic aluminum oxide is introduced as a solid phase base for the one step synthesis of 2-isoxazolines from aldoximes and olefins. An X-ray diffraction study of compound $\text{13c}$ verifies the stereochemical assignments.