title: Total synthesis of lamellarins D, H, and R and ningalin B.
abstract: A concise total synthesis of lamellarins D (7 steps), H (7 steps), and R (5 steps) and ningalin B (5 steps) is achieved starting from the corresponding aldehydes and amines. The synthesis features three oxidative reactions as key steps in a biomimetic manner, involving an AgOAc-mediated oxidative coupling reaction to construct the pyrrole core, a Pb(OAc)(4)-induced oxidative cyclization to form the lactone, and Kita's oxidation reaction to form the pyrrole-arene C-C bond.
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, 38 Xueyuan Road, Beijing 100191, China.
authors.forename: Qingjiang
authors.initials: Q
authors.lastname: Li
authors.forename: Jingqian
authors.initials: J
authors.lastname: Jiang
authors.forename: Aili
authors.initials: A
authors.lastname: Fan
authors.forename: Yuxin
authors.initials: Y
authors.lastname: Cui
authors.forename: Yanxing
authors.initials: Y
authors.lastname: Jia
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D002384:Catalysis; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D008386:Marine Biology; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000447:Aldehydes; D000470:Alkaloids; D000588:Amines; D003374:Coumarins; D006575:Heterocyclic Compounds, 3-Ring; D006576:Heterocyclic Compounds, 4 or More Rings; D007546:Isoquinolines; D011758:Pyrroles; C455554:lamellarin D; C455555:lamellarin H; C556204:lamellarin R; C409782:ningalin B