Synthesis of the N-Acyl Amycolose Moiety of Amycolamicin and Its Methyl Glycosides

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Abstract

The N-acyl amycolose moiety incorporated in amycolamicin, a broad-spectrum antibacterial natural product produced by soil actinomycetes, and its two anomeric methyl glycosides have been synthesized enantioselectively each in 12 steps from a known methyl (R)-lactate derivative by exploiting a diastereoselective nucleophilic addition of a p-methoxybenzyloxy-substituted vinyllithium reagent to an α,β-bisalkoxy ketone intermediate to provide the corresponding tertiary alcohol as a single diastereomer. The three sugar derivatives are known as cytotoxic degradation products of amycolamicin.

Original languageEnglish
Pages (from-to)7474-7479
Number of pages6
JournalJournal of Organic Chemistry
Volume84
Issue number11
DOIs
Publication statusPublished - 2019 Jun 7

ASJC Scopus subject areas

  • Organic Chemistry

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