Convenient synthesis of substituted piperidinones from alpha,beta-unsaturated amides: formal synthesis of deplancheine, tacamonine, and paroxetine.
[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.
Takasu
Kiyosei
K
Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578, Japan.
Nishida
Naoko
N
Tomimura
Akiko
A
Ihara
Masataka
M
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
D000577:Amides; D018687:Antidepressive Agents, Second-Generation; D026121:Indole Alkaloids; D010880:Piperidines; C496494:deplancheine; C449743:tacamonine; D017374:Paroxetine