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Stereochemical Determination of Tuscolid/Tuscorons and Total Synthesis of Tuscoron D and E: Insights into the Tuscolid/Tuscoron Rearrangement
Author(s) -
Göricke Björn,
Bieber Michelle Fernandez,
Mohr Kathrin E.,
Menche Dirk
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201906166
Subject(s) - chemistry , derivatization , total synthesis , cope rearrangement , stereochemistry , combinatorial chemistry , mass spectrometry , chromatography
The stereochemistry of the structurally unique myxobacterial polyketides tuscolid/tuscorons was determined by a combination of high‐field NMR studies, molecular modeling, and chemical derivatization and confirmed by a modular total synthesis of tuscorons D and E. Together with the discovery of three novel tuscorons, this study provides detailed insight into the chemically unprecedented tuscolid/tuscoron rearrangement cascade.