title: Divergent total syntheses of (-)-lycopladine D, (+)-fawcettidine, and (+)-lycoposerramine Q.
abstract: Enantioselective total syntheses of (+)-fawcettidine and (+)-lycoposerramine Q as well as the first total synthesis of (-)-lycopladine D from a common intermediate have been accomplished by a divergent path. The common intermediate was derived from a Hajos-Parrish-like diketone by a stereoselective Birch reduction and a Suzuki coupling. The synthesis of (-)-lycopladine D featured an allylic oxidation and a biomimetic aminoketalization while the route to (+)-fawcettidine and (+)-lycoposerramine Q highlighted an oxidative rearrangement.
authors.affiliation: Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
authors.forename: Chen
authors.initials: C
authors.lastname: Zeng
authors.forename: Changwu
authors.initials: C
authors.lastname: Zheng
authors.forename: Jingyun
authors.initials: J
authors.lastname: Zhao
authors.forename: Gang
authors.initials: G
authors.lastname: Zhao
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D006575:Heterocyclic Compounds, 3-Ring; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D006575:Heterocyclic Compounds, 3-Ring; D012717:Sesquiterpenes; C524731:fawcettimine; C587751:lycopladine D; C587313:lycoposerramine-Q