title: Enantioselective total syntheses of leuconolam-leuconoxine-mersicarpine group monoterpene indole alkaloids.
abstract: A unified strategy allowing enantioselective total syntheses of (-)-mersicarpine, (-)-scholarisine G, (+)-melodinine E, (-)-leuconoxine, and (-)-leuconolam from a common cyclohexenone derivative was reported. The Suzuki-Miyaura reaction was used to couple two simple fragments incorporating the key elements for total synthesis, and unprecedented oxidation/reduction/cyclization processes were developed that converted the substituted cyclohexenone to either a mersicarpine or leuconoxine skeleton. In a reverse biomimetic synthesis fashion, (+)-melodinine E was converted to (-)-leuconolam under acidic conditions.
authors: Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne , EPFL-SB-ISIC-LSPN, BCH 5304, CH-1015 Lausanne, Switzerland.
authors: Zhengren
authors: Z
authors: Xu
authors: Qian
authors: Q
authors: Wang
authors: Jieping
authors: J
authors: Zhu
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D001381:Azepines / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D026121:Indole Alkaloids / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D039821:Monoterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D001381:Azepines; D026121:Indole Alkaloids; D039821:Monoterpenes; C000590191:leuconoxine; C529544:mersicarpine; C062173:leuconolam