A regiodivergent synthesis of ring a C-prenylflavones.
Capitalizing on the use of orthogonal protecting groups and the development of a modified Robinson flavone synthesis that avoids harsh acidic conditions, a regioselective synthesis of 6- and 8-prenylflavones from the same prenylated disilylated phloracetophenone (9) has been developed, targeting cannflavin B (1d), the COX-inhibiting principle of marijuana, and its unnatural isomer isocannflavin B (1e) as model compounds.
Minassi
Alberto
A
Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche, Università del Piemonte Orientale, Novara, Italy.
Giana
Anna
A
Ech-Chahad
Abdellah
A
Appendino
Giovanni
G
D002188:Cannabis / Q000737:chemistry; D016861:Cyclooxygenase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D047309:Flavones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011451:Prostaglandin-Endoperoxide Synthases / Q000737:chemistry; D013237:Stereoisomerism
D016861:Cyclooxygenase Inhibitors; D047309:Flavones; D011451:Prostaglandin-Endoperoxide Synthases