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Total Synthesis of Mycinamicin IV as Integral Part of a Collective Approach to Macrolide Antibiotics
Author(s) -
Späth Georg,
Fürstner Alois
Publication year - 2022
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202104400
Subject(s) - aglycone , context (archaeology) , blueprint , total synthesis , glycosylation , core (optical fiber) , antibiotics , macrolide antibiotics , combinatorial chemistry , chemistry , computer science , stereochemistry , biology , engineering , biochemistry , mechanical engineering , paleontology , telecommunications , erythromycin , glycoside
Abstract The total synthesis of the 16‐membered macrolide mycinamicin IV is outlined, which complements our previously disclosed, largely catalysis‐based route to the aglycone. This work must also be seen in the context of our recent conquest of aldgamycin N, a related antibiotic featuring a similar core but a distinctly different functionalization pattern. Taken together, these projects prove that the underlying blueprint is integrative and hence qualifies for a collective approach to this prominent class of natural products. In both cases, the final glycosylation phase mandated close attention and was accomplished only after robust de novo syntheses of the (di)deoxy sugars of the desosamine, chalcose, mycinose and aldgarose types had been established. Systematic screening of the glycosidation promoter was also critically important for success.