Stereochemical Determination of Tuscolid/Tuscorons and Total Synthesis of Tuscoron D and E: Insights into the Tuscolid/Tuscoron Rearrangement | Zendy

Göricke Björn | Zendy; Bieber Michelle Fernandez | Zendy; Mohr Kathrin E. | Zendy; Menche Dirk | Zendy

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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.

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