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Five‐Step Synthesis of Yaequinolones J1 and J2

preprint
submitted on 12.12.2019 and posted on 18.12.2019 by Johannes Schwan, Merlin Kleoff, Philipp Heretsch, Mathias Christmann
A concise synthesis of yaequinolones J1 and J2 is reported. The route is based on the aryne insertion into the σ- C–N-bond of an unsymmetric imide followed by a diastereoselective aldol cyclization of the resulting N-acylated aminobenzophenone. The chromene motif is generated in the first step by an organocatalytic tandem Knoevenagel-electrocyclization of citral and 2-bromoresorcinol. The approach adheres to the ideality-principle, using almost exclusively strategic bond-forming
reactions.

History

Email Address of Submitting Author

mathias.christmann@fu-berlin.de

Institution

Freie Universität Berlin

Country

Germany

ORCID For Submitting Author

0000-0001-9313-2392

Declaration of Conflict of Interest

No conflict of interest

Version Notes

Version 1.0

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in Organic Letters

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