Journal of the Chemical Society. Perkin transactions I p. 787 - 798 (1989)
Update date:2022-08-04
Topics:
Fishman, Andrew G.
Mallams, Alan K.
Rossman, Randall R.
Selective acylation techniques have been developed that enable the synthesis of 3-O-acetyl-4''-O-isovaleryltylosin and 3-O-acetyl-23-O-demycinosyl-4''-O-isovaleryltylosin to be carried out in an efficient manner starting from tylosin.The syntheses of the 2'-O-acetyl, 23-O-acetyl, and 2',23-di-O-acetyl derivatives of the latter are also described.The synthesis of key hydrazones is also described.The regio- and stereo-selective epoxidation of tylosin and its acyl derivatives afforded the 12,13-epoxyanalogues, which were used to synthesize novel acylated 12,13-epoxy derivatives of 23-O-demycinosyltylosin.
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