Short synthesis of noscapine, bicuculline, egenine, capnoidine, and corytensine alkaloids through the addition of 1-siloxy-isobenzofurans to imines

Autor:	Maria Del Pilar C. Soriano, Nagula Shankaraiah, Leonardo S. Santos
Rok vydání:	2010
Předmět:	Organic Chemistry Imine Diastereomer Iminium Total synthesis Biochemistry Adduct Noscapine chemistry.chemical_compound chemistry Drug Discovery Ionic liquid medicine Organic chemistry Amine gas treating medicine.drug
Zdroj:	TETRAHEDRON LETTERS Artículos CONICYT CONICYT Chile instacron:CONICYT
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2010.01.104
Popis:	A concise diastereotioselective strategy for the synthesis of noscapine, bicuculline, and egenine ( 1a – c ), as well as capnoidine and corytensine ( 2a , b ), was developed using diastereoselective addition of 1-siloxy-isobenzofurans 4a and 4b to iminium ion 5 in a one-pot approach. The synthesis features the use of imine 13 obtained through Bischler–Napieralsky reaction from amine 11 . The addition of ionic liquids as addictives in the reactions afforded erythro configuration in major adduct compounds. The synthetic route can also be applied in the total synthesis of promising tubulin binding agent EM105 ( 3 ).
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::feb59be71cbafa67553e637e96ba327c https://doi.org/10.1016/j.tetlet.2010.01.104 Zobrazit plný text záznamu Full Text from ScienceDirect