Regiospecific O → N Acyl Migration as a Methodology to Access l-Altropyranosides with an N 2, N 4-Differentiation

Org Lett. 2022 Dec 2;24(47):8667-8671. doi: 10.1021/acs.orglett.2c03508. Epub 2022 Nov 16.


Pseudaminic acid and its biosynthetic altropyranoside precursors are bacterial components currently being investigated toward novel antibacterial strategies. One structural feature associated with these naturally occurring flagellar carbohydrates is the different N-acylation patterns on the two amido functionalities, posing a synthetic challenge. A new one-pot methodology is reported and a scope of diverse N2/N4-differentiated analogs are presented via a Staudinger reduction-mediated regiospecific O3 → N4 acyl migration, followed by an autonomous N2-acylation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acylation*