title: A General, Concise Strategy that Enables Collective Total Syntheses of over 50 Protoberberine and Five Aporhoeadane Alkaloids within Four to Eight Steps.
abstract: A concise, catalytic, and general strategy that allowed efficient total syntheses of 22 natural 13-methylprotoberberines within four steps for each molecule is reported. This synthesis represents the most efficient and shortest route to date, featuring three catalytic processes: CuI-catalyzed redox-A(3) reaction, Pd-catalyzed reductive carbocyclization, and PtO2 -catalyzed hydrogenation. Importantly, this new strategy to the tetracyclic framework has also been applied to the collective concise syntheses of >30 natural protoberberines (without 13-methyl group) and five aporhoeadane alkaloids.
authors.affiliation: Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China.
authors.forename: Shiqiang
authors.initials: S
authors.lastname: Zhou
authors.affiliation: Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China. rtong@ust.hk.
authors.forename: Rongbiao
authors.identifier: 0000-0002-2740-5222
authors.initials: R
authors.lastname: Tong
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001552:Benzazepines / Q000138:chemical synthesis* / Q000737:chemistry; D001600:Berberine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006865:Hydrogenation; D008958:Models, Molecular; D010084:Oxidation-Reduction; D010087:Oxides / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D010984:Platinum / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D001552:Benzazepines; D001600:Berberine Alkaloids; D010087:Oxides; C514637:platinum oxide; C009090:protoberberine; D010984:Platinum; D010165:Palladium
keywords: 13-methylprotoberberine; aporhoeadane; protoberberine; redox-A3 reaction; total synthesis