title: Total synthesis of securinega alkaloids (-)-norsecurinine, (-)-niruroidine and (-)-flueggine A.
abstract: A consecutive synthetic strategy was developed toward the total synthesis of securinega alkaloids. (-)-Norsecurinine was concisely assembled by addition of a methoxyallene to a ketone for efficient side-chain installation. Ring-closing metathesis was also utilized as a key step. The first total synthesis of (-)-niruroidine was achieved from (-)-norsecurinine in three steps, while the route to (-)-flueggine A featured a 1,3-dipolar cycloaddition to forge the core structure.
authors.affiliation: Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, PR China. chyewc@gmail.com.
authors.forename: Nan
authors.initials: N
authors.lastname: Ma
authors.forename: Yiwu
authors.initials: Y
authors.lastname: Yao
authors.forename: Bing-Xin
authors.initials: BX
authors.lastname: Zhao
authors.forename: Ying
authors.initials: Y
authors.lastname: Wang
authors.forename: Wen-Cai
authors.initials: WC
authors.lastname: Ye
authors.forename: Sheng
authors.initials: S
authors.lastname: Jiang
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D001381:Azepines / Q000138:chemical synthesis*; D061565:Cycloaddition Reaction; D019665:Euphorbiaceae / Q000737:chemistry*; D007212:Indolizines / Q000138:chemical synthesis*; D010880:Piperidines / Q000138:chemical synthesis*
chemical_list: D000470:Alkaloids; D001381:Azepines; D007212:Indolizines; D010880:Piperidines; C568567:flueggine A; C000597366:niruroidine; C050244:norsecurinine