Asymmetric synthesis of yohimban alkaloids. Total synthesis of (-)-pseudo- and (-)-alloyohimban

Autor:	Albert I. Meyers, Thomas K. Highsmith, Paul T. Buonora
Rok vydání:	1991
Předmět:	Indole test chemistry.chemical_compound Intramolecular reaction Diene chemistry Stereochemistry Yohimban Organic Chemistry Enantioselective synthesis Total synthesis Enantiomer Cycloaddition
Zdroj:	The Journal of Organic Chemistry. 56:2960-2964
ISSN:	1520-6904 0022-3263
Popis:	A route to (−)-pseudo and (−)-allo isomers of yohimban is described. This asymmetric synthetic approach to indole alkaloids is based on the stereocontrolled alkylation of α-amino carbanions mediated by chiral formamidines. The stereochemically pure enantiomer of the alkylated β-carboline 7 is utilized to bias the subsequent intramolecular Diels-Alder cycloaddition of the N-dienamide 8 or the homologous N-acrylamide 12 derived from the alkylated carboline 11. In this fashion, suitable choice of diene and dienophile partners led to the pseudo- and alloyohimban isomers 1b and 1c, respectively
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::2c0b4d32ecd119b827aa5c027ad539eb https://doi.org/10.1021/jo00009a007 Zobrazit plný text záznamu