Novel route to 5-position vinyl derivatives of thiolactomycin: Olefination vs. deformylation
Pilho Kim1, Clifton E Barry, Cynthia S Dowd
1Tuberculosis Research Section, National Institute of Allergy and Infectious Diseases, National Institutes of Health, Rockville, MD 20852.
Abstract:
Vinyl and diene derivatives of thiolactomycin have been prepared via Horner-Wadsworth-Emmons olefination from protected 5-formyl-3,5-dimethylthiotetronic acid. Several 4-position protecting groups and a variety of phosphonates were evaluated, with MOM protection and beta-ketophosphonates yielding the highest ratio of desired product to deformylated product.
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