Practical Synthesis of Iboxamycin, a Potent Antibiotic Candidate, in Amounts Suitable for Studies in Animal Infection Models
semanticscholar(2021)
摘要
A gram-scale
synthesis of iboxamycin, an antibiotic candidate bearing a fused bicyclic amino
acid residue, is presented. A pivotal transformation in the route involves an
intramolecular hydrosilylation–oxidation sequence to set the ring-fusion
stereocenters of the bicyclic scaffold. Other notable features of the synthesis
include a high-yielding, highly diastereoselective alkylation of a
pseudoephenamine amide, a convergent sp3–sp2 Negishi
coupling, and a one-pot transacetalization–reduction reaction to form the
target compound’s oxepane ring. Implementation of this synthetic strategy has
provided ample quantities of iboxamycin to allow for its in vivo profiling in murine models of infection.
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