Concise synthesis of prenylated and geranylated chalcone natural products by regiospecific iodination and Suzuki coupling reactions

Molecular Characterization and Phylogenetic Analysis of Two Novel Regio-specific Flavonoid Prenyltransferases from Morus alba and Cudrania tricuspidata

“…S2). The NMR data of 1a were in good agreement with those of 3Ј-dimethylallyl isoliquiritigenin (31,32). Therefore, the enzymatic product of MaIDT was unambiguously identified as 3Ј-dimethylallyl isoliquiritigenin (1a), which indicates that this enzyme regiospecifically transferred a dimethylallyl moiety to 1 at the C-3Ј position; thus, this recombinant enzyme was designated as MaIDT (M. alba isoliquiritigenin 3Ј-dimethylallyltransferase).…”

Synthesis and in Vitro Antifungal Activity against Botrytis cinerea of Geranylated Phenols and Their Phenyl Acetate Derivatives

“…Compounds 6 – 24 (see Figure 2 ) were synthesized through the electrophilic aromatic substitution reaction (EAS), which proceeds by the slow addition of geraniol to a solution of phenol derivatives in dioxane and in the presence of BF 3 ·Et 2 O which acts as catalyst [ 1 , 6 , 10 , 11 ]. This reaction was chosen, between many different synthetic pathways for obtaining prenylated compounds [ 1 , 11 , 12 , 13 , 14 ], because it has been previously used to synthesize a series of synthetic analogs of 3-demethylubiquinone ( 3 ) having one, two, or three methoxy groups in different positions of the quinone moiety [ 6 ]. Alternatively, the reaction was also carried out in acetonitrile instead of dioxane, using AgNO 3 as a secondary catalyst [ 9 ].…”

Functionalized cyclopentenes through a tandem NHC-catalyzed dynamic kinetic resolution and ambient temperature decarboxylation: mechanistic insight and synthetic application

“…To the best of our knowledge, a general catalytic asymmetric variant to these compounds has not been reported. The formal synthesis began with the treatment of literature known 9 acetophenone 4 with dimethyl carbonate and sodium hydride in toluene afforded β-keto ester 5. A Tsuji-Trost allylation of β-ketoester and with allyl carbonate 6 and subsequent PCC oxidation provided aldehyde 7 in 36% yield over three steps.…”