112389-35-2Relevant articles and documents
Novel Semisynthetic Oxo and Alkyl Macrolide Antibacterials and Related Derivatives
Fishman, Andrew G.,Mallams, Alan K.,Puar, Mohindar S.,Rossman, Randall R.,Stephens, Richard L.
, p. 1189 - 1210 (2007/10/02)
An efficient method of protecting the 10,11-double bond in dienone and epoxy enone 16-membered macrolides has been developed.This involves Michael addition of thioacetic S-acid to the 10,11-ene to give exclusively the 11-acetylthio derivatives, which can be smoothly deprotected by treatment with fluoride ion.The protected intermediates have been used to prepare a novel class of macrolide antibacterials in which the aldehyde group has been converted into an alkyl ketone by reaction with the appropriate diazoalkane.Thus 20-oxo analogues of rosaramicin, 12,13-de-epoxy-12,13-dehydro-rosaramicin, tylosin, and desmycosin have been prepared.The reaction of diazomethane with unprotected macrolides has also been studied including the synthesis of 18-C-methyl-3''-O-propionyl-leucomycin A5.Derivatives in which the 20-formyl group has been replaced by metal and by halogeno groups, as well as derivatives having a 2,3-ene are described.A number of base-catalyzed rearrangement products including desmycosin 8β,20α-aldol and desmycosin 8α,20β-aldol are also described.
