Synthetic studies on bafilomycin A1: stereoselective synthesis of the C12–C17 fragment and its coupling with the C1–C11 subunit

Autor:	Robert Lett, Emmanuelle Queron
Rok vydání:	2004
Předmět:	chemistry.chemical_classification Chemistry Stereochemistry Carboxylic acid Organic Chemistry Bafilomycin Biochemistry Aldehyde Adduct Stille reaction chemistry.chemical_compound Enantiopure drug Intramolecular force Drug Discovery Stereoselectivity
Zdroj:	Tetrahedron Letters. 45:4533-4537
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2004.04.034
Popis:	Stereoselective addition of ( E )-1-lithio-2-tributylstannylethylene on a chiral cyclic di- t -butylsilyleneketal C 14 –C 17 aldehyde afforded the required Felkin–Anh adduct for the synthesis of the C 12 –C 17 fragment of bafilomycin A 1 , the configuration of which was assigned unambiguously. After appropriate coupling with the enantiopure C 1 –C 11 fragment, the C 12 –C 17 subunit obtained here can be used for the study of the 16-membered macrolide formation either by an acyl activation or an intramolecular Stille reaction. Intermolecular esterification of the 15-OH with an acyl activation of the carboxylic acid of the C 1 –C 11 fragment, in modified Yamaguchi's conditions, affords here an intermediate for examining an intramolecular Stille coupling.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::82c7b78eca8e7a555f5fb55bb2521d2c https://doi.org/10.1016/j.tetlet.2004.04.034 Zobrazit plný text záznamu Full Text from ScienceDirect