Novel route to 5-position vinyl derivatives of thiolactomycin: Olefination vs. deformylation.
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.
Kim
Pilho
P
Tuberculosis Research Section, National Institute of Allergy and Infectious Diseases, National Institutes of Health, Rockville, MD 20852.
Barry
Clifton E
CE
Dowd
Cynthia S
CS