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Five‐Step Synthesis of Yaequinolones J1 and J2
preprintsubmitted on 12.12.2019, 16:35 and posted on 18.12.2019, 13:08 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
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in Organic Letters