title: Convenient synthesis of substituted piperidinones from alpha,beta-unsaturated amides: formal synthesis of deplancheine, tacamonine, and paroxetine.
abstract: [reaction: see text] An intermolecular aza-double Michael reaction leading to functionalized piperidin-2-ones from simple starting materials has been developed. The method allows alpha,beta-unsaturated amides to be used as a synthon of the piperidine nucleus. In addition, the utility of this methodology is demonstrated by its application to a formal synthesis of the indolo[2,3-a]quinolizidine alkaloids, (+/-)-deplancheine, (+/-)-tacamonine, and the antidepressant paroxetine.
authors.affiliation: Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578, Japan.
authors.forename: Kiyosei
authors.initials: K
authors.lastname: Takasu
authors.forename: Naoko
authors.initials: N
authors.lastname: Nishida
authors.forename: Akiko
authors.initials: A
authors.lastname: Tomimura
authors.forename: Masataka
authors.initials: M
authors.lastname: Ihara
mesh_terms: D000577:Amides / Q000737:chemistry*; D018687:Antidepressive Agents, Second-Generation / Q000138:chemical synthesis; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D017374:Paroxetine / Q000138:chemical synthesis* / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis; D013237:Stereoisomerism
chemical_list: D000577:Amides; D018687:Antidepressive Agents, Second-Generation; D026121:Indole Alkaloids; D010880:Piperidines; C496494:deplancheine; C449743:tacamonine; D017374:Paroxetine