Total Synthesis of Biologically Active Natural Products with 6hdibenzo[B,D]Pyran-6-One Using Palladium Catalyzed Biaryl Coupling Reactions

Ishtiaq Jeelani, Hitoshi Abe, Katsunori Itay 1

8th WCPSDM.2021. APR.Published Online 18 APR 2021

Abstract : A variety of natural products, which possess the 6H-dibenzo[b,d]pyran-6-one core has attracted our interest because of their unique biological activities. A palladium-mediated intramolecular aryl-aryl coupling reaction was applied to the total synthesis of the bioactive natural products, Hyalodedriol C, and Urolithin C 3-Glucuronide, which possess 6H-dibenzo[b,d]pyran-6-one skeleton. These compounds are known to be a naturally occurring bioactive compound that possesses potential biological properties like antifungal, antibacterial, antioxidant, larvicidal, anti-inflammatory and anticancer properties. The interesting structural feature of hyalodendriol C is the aromatic ring bearing chlorine atom on it. Natural products comprising a halogen on an olefinic, aromatic, heteroaromatic moieties as a substituent have gained considerable interest because of their multiple biological activities. Keeping in view, the indispensable biological values of these compounds, we took the advantage of our established strategy to chemically synthesize hyalodedriol C, and Urolithin C 3-Glucuronide. We have reported several natural product syntheses using the Pd-mediated intramolecular biaryl coupling reaction6 with phenyl benzoate derivatives for forming the 6H-dibenzo[b,d]pyran-6-one ring system. Utilizing this transformation, we planned the efficient syntheses of hyalodedriol C, and Urolithin C 3-Glucuronide.