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Synthesis of Chloro-Substituted 6H-Dibenzo[b,d]pyran-6-one Natural Products, Graphislactone G, and Palmariols A and B
Chemical & Pharmaceutical Bulletin  (IF1.645),  Pub Date : 2021-08-01, DOI: 10.1248/cpb.c21-00316
Hitoshi Abe, Ishtiaq Jeelani, Atsuro Yonoki, Haruka Imai, Yoshikazu Horino

A palladium-mediated intramolecular aryl–aryl coupling reaction was applied to the total synthesis of the bioactive natural products, graphislactone G (1), and palmariols A (2) and B (3), which possess an unusual chloro-subsutituent on the 6H-dibenzo[b,d]pyran-6-one skeleton. Based on the transition state model of the coupling reaction, the mechanistic aspect for the regioselectivity of the aryl–aryl coupling reaction is also discussed.

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