Total Synthesis of the Natural Carbazoles Glycozolicine, Mukoline, and Mukolidine, Starting from 4,5-Dimethyleneoxazolidin-2-ones

Autor:	Joaquín Tamariz, Rafael Bautista, Luisa E. Montiel, Pablo Bernal, Francisco Delgado
Rok vydání:	2011
Předmět:	chemistry.chemical_compound chemistry Cascade reaction Yield (chemistry) Organic Chemistry Organic chemistry Total synthesis Regioselectivity Alcohol Chemical synthesis Catalysis Cycloaddition Methyl group
Zdroj:	Synthesis. 2011:929-933
ISSN:	1437-210X 0039-7881
Popis:	A novel and efficient synthesis of naturally occurring 1-methoxycarbazoles glycozolicine, mukolidine, and mukoline is developed by applying a regioselective Diels-Alder reaction of a 4,5-dimethyleneoxazolidin-2-one with acrolein. The cycloadduct is transformed to the corresponding functionalized diarylamine. The key palladium-catalyzed cyclization/deformylation cascade reaction of the latter leads to glycozolicine in high overall yield. Oxidation of the C6 methyl group provides the 6-formylcarbazole mukolidine, which is reduced to the respective natural alcohol mukoline.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::963008bcc091b0102f46dec4587e4ead https://doi.org/10.1055/s-0030-1258444 Zobrazit plný text záznamu