Abstract
The design and synthesis of novel 15-membered 11-azalides and 16-membered 11,12-diazalide starting from 16-membered macrolides are reported. A mobile linear dialdehyde was isolated via a cyclic tetraol which was prepared by osmium oxidation of a conjugated diene. One-pot macrocyclization of this dialdehyde with an amine or a diamine afforded corresponding 15-membered azalides or 11,12-diazalide. Fundamental SAR studies of 15-membered 11-azalides disclosed their potentiality as a lead molecule for further chemical modifications. For environmental preservation, sustainable chemistry for synthesis of these azalides is also discussed.
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Miura, T., Natsume, S., Kanemoto, K. et al. Novel Azalides Derived from Sixteen-Membered Macrolides. J Antibiot 60, 407–435 (2007). https://doi.org/10.1038/ja.2007.55
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DOI: https://doi.org/10.1038/ja.2007.55
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