title: Total synthesis of (-)-goniomitine.
abstract: The total synthesis of (-)-goniomitine has been accomplished in 11 steps starting from commercially available diethyl l-malate. The synthesis features a chiral pool approach to prepare the chiral C-9 unit containing a quaternary carbon center, an Ir-catalyzed C-H borylation to synthesize the 2-indoleboronic acid pinacol ester, and a Suzuki reaction to couple together the two key intermediates. Notably, the high degree of convergence of this strategy makes it particularly amenable to the total synthesis of other aspidosperma family natural products.
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University , 38 Xueyuan Road, Beijing 100191, China.
authors.forename: Shiqiang
authors.initials: S
authors.lastname: Zhou
authors.forename: Yanxing
authors.initials: Y
authors.lastname: Jia
mesh_terms: D030009:Aspidosperma / Q000737:chemistry; D002384:Catalysis; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D008293:Malates / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D026121:Indole Alkaloids; D008293:Malates; C526621:goniomitine; C058705:diethyl malate