Custom synthesis of substituted butenolides, dihydropyranones, and α-E-alkylidenelactones via alkenylalumination

Autor:	Garrett Garner, P. Veeraraghavan Ramachandran, Debarshi Pratihar, B. China Raju
Rok vydání:	2011
Předmět:	chemistry.chemical_compound Stereospecificity chemistry Yield (chemistry) Organic Chemistry Drug Discovery Trifluoroacetic acid Biochemistry Medicinal chemistry Conjugate
Zdroj:	Tetrahedron Letters. 52:4985-4988
ISSN:	0040-4039
Popis:	Alkenylalumination of aldehydes with [α-(ethoxycarbonyl)-β-(t-butyldimethylsilyloxyalkyl)alkenyl]diisobutylaluminum provides the corresponding α-Z-alkylidene-β′-hydroxy esters, which upon protection and treatment with trifluoroacetic acid lactonizes to furnish α-acetoxyalkyl butenolides (n = 1) and dihydropyranones (n = 2) in 40% overall yield. Conjugate addition to these lactenones and concurrent acetate elimination constitute a general and stereospecific synthesis of the corresponding α-E-alkylidene lactones.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::5b714096a7222c716213109bcff91d16 https://doi.org/10.1016/j.tetlet.2011.06.103 Zobrazit plný text záznamu Full Text from ScienceDirect