ASYMMETRIC-SYNTHESIS OF THE LEFT HAND PORTION OF THE AZINOMYCINS

A nine step synthesis of the left hand portion of the azinomycins is d escribed starting from 3,3-dimethylacrylic acid. The approach relies o n a Sharpless asymmetric dihydroxylation (AD) reaction to install the requisite (2S,3S)-stereochemistry of epoxy alcohol 4. This epoxide is converted to crystalline amide derivative 12 whose structure and absol ute stereochemistry have been unambiguously established using X-ray cr ystallography, Coupling of epoxy alcohol (2S,3S)-4 with naphthoyl chlo ride 16 and subsequent manipulations furnish epoxy amide (2S,3S)-1 ide ntical in all respects with the natural material.