Intramolecular Diels–Alder reactions of oxazole–olefins: synthesis of the Rauwolfia alkaloids suaveoline and norsuaveoline

Autor:	Masashi Ohba, Itaru Natsutani, Takashi Sakuma
Rok vydání:	2007
Předmět:	Indole test Stereochemistry Chemistry Organic Chemistry Total synthesis Biochemistry chemistry.chemical_compound Rauwolfia alkaloid Intramolecular force Drug Discovery Pyridine Organic chemistry Derivative (chemistry) Diels–Alder reaction Oxazole
Zdroj:	Tetrahedron. 63:10337-10344
ISSN:	0040-4020
DOI:	10.1016/j.tet.2007.07.070
Popis:	A full account of the highly stereoselective total synthesis of two indole alkaloids, suaveoline ( 4 ) and norsuaveoline ( 5 ), is presented. Central features of the synthetic strategy include the conversion of l -tryptophan methyl ester ( 12 ) into the oxazole derivative 11 and the intramolecular Diels–Alder reaction of the oxazole–olefin 19 leading to the pentacyclic pyridine derivative 21 .
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::ee371b093ee47c4319f1988a0258e366 https://doi.org/10.1016/j.tet.2007.07.070 Zobrazit plný text záznamu Full Text from ScienceDirect