Copper mediated scalemic organolithium reagents in alkaloid syntheses

Autor:	Ningyi Chen, R. Karl Dieter, Rhett T. Watson
Rok vydání:	2005
Předmět:	Stereochemistry Alkaloid Organic Chemistry Halide Indolizidine Biochemistry chemistry.chemical_compound Deprotonation chemistry Intramolecular force Reagent Drug Discovery Pyrrolizidine Functional group
Zdroj:	Tetrahedron. 61:3221-3230
ISSN:	0040-4020
DOI:	10.1016/j.tet.2005.01.094
Popis:	Scalemic 2-pyrrolidinylcuprates generated via asymmetric deprotonation of N-Boc-pyrrolidine followed by treatment with THF soluble CuCN·2LiCl react with ω-functionalized vinyl halides to afford 2-alkenyl-N-Boc-pyrrolidines. N-Boc deprotection and cyclization via intramolecular N-alkylation generates the pyrrolizidine or indolizidine skeletons. Subsequent functional group manipulation affords enantioenriched (+)-heliotridane, (+)-isoretronecanol, a formal synthesis of (+)-laburnine, (+)-(R)-2,3,5,7a-tetrahydro-1H-pyrrolizine, (R)-1,2,3,5,6,8a-hexahydroindolizine, (+)-ent-δ-coniceine, (+)-tashiromine and (+)-5-epitashiromine.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::f959f48420546becdf9f98cb47c04a48 https://doi.org/10.1016/j.tet.2005.01.094 Zobrazit plný text záznamu Full Text from ScienceDirect