Convenient synthesis of substituted piperidinones from alpha,beta-unsaturated amides: formal synthesis of deplancheine, tacamonine, and paroxetine.

Autor: Takasu K; Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578, Japan., Nishida N, Tomimura A, Ihara M
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2005 May 13; Vol. 70 (10), pp. 3957-62.
DOI: 10.1021/jo050261x
Abstrakt: [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.
Databáze: MEDLINE