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Updated: Mar 18, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Stereoselective Synthesis of Elaborate Fragments of Vancoresmycin and Amycomycin Enable Full Stereochemical
Max Schönenbroicher1, Maximilian Seul1, Simon Morgenschweis1
1Kekulé-Institute for Organic Chemistry and Biochemistry, University of Bonn, D-53121 Bonn, Germany.
Abstract:
Efficient syntheses of three elaborate fragments of the complex polyketide antibiotics vancoresmycin and amycomycin were accomplished by concise strategies including various boron mediated couplings, an innovative Cu-catalyzed β-boration as well as a highly diastereoselective glycosylation, allowing for a convergent assembly of densely functionalized subunits with excellent diastereoselectivity. Comparative NMR analyses allow full configurational assignment of these potent antimicrobial agents including determination of six previously unknown centers, thus resolving previous contradictory proposals and validating the Kalesse/Kitsche profile hidden Markov model (pHMM) as a reliable tool for predicting hydroxyl- and methyl-bearing stereocenters.
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