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Five-Step Synthesis of Yaequinolones J1 and J2

J. Schwan, M. Kleoff, P. Heretsch, M. Christmann – 2020

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.

Title
Five-Step Synthesis of Yaequinolones J1 and J2
Author
J. Schwan, M. Kleoff, P. Heretsch, M. Christmann
Date
2020
Identifier
DOI: 10.1021/acs.orglett.9b04455
Citation
Org. Lett. 2020, 22, 675–678.