Tetrahedron letters

Novel route to 5-position vinyl derivatives of thiolactomycin: olefination versus deformylation

P Kim, CE Barry, CS Dowd

Index: Kim, Pilho; Barry III, Clifton E.; Dowd, Cynthia S. Tetrahedron Letters, 2006 , vol. 47, # 20 p. 3447 - 3451

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Citation Number: 9

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 β-ketophosphonates yielding the highest ratio of the desired product to deformylated product.