Abstract
The stereochemical course of the 1,2-addition upon treatment of various 1-thio-4-oxo sugars with McMgXand McLi has been determined. The effects of reagent, solvent, and neighboring functionalities in the gluco/galacto (non-chelation/chelation controlled) product distribution are detailed. Stereocontrolled 1,2-addition to these 4-oxo sugars provide access to a number of differently functionalized F unit building blocks of the moenomycin family, and demonstrate the versatility of this transformation.
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