Co-catalyzed two-stereocentered hydrolytic kinetic resolution: application to the synthesis of yashabushidiols A and B and the lactone unit of compactin and mevinolin

Autor:	Sunita K. Gadakh, Arumugam Sudalai
Rok vydání:	2015
Předmět:	chemistry.chemical_classification Electrophilic addition Chemistry Organic Chemistry Enantioselective synthesis Epoxide Catalysis Kinetic resolution Inorganic Chemistry chemistry.chemical_compound Intramolecular force Moiety Organic chemistry Physical and Theoretical Chemistry Enantiomer Lactone
Zdroj:	Tetrahedron: Asymmetry. 26:118-123
ISSN:	0957-4166
DOI:	10.1016/j.tetasy.2014.12.006
Popis:	A short and efficient enantioselective synthesis of yashabushidiols A and B and the β-hydroxy-δ-lactone moiety of compactin and mevinolin with high enantiomeric purity (98% ee) is described starting from commercially available materials. The strategy mainly comprises of iodine-induced intramolecular electrophilic addition of a carbonate occurring in a highly diastereoselective fashion and the Co-catalyzed two-stereocentered hydrolytic kinetic resolution of a functionalized epoxide as the chiral inducing step.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::b5b9d68aea29954a2d6da92f3f0ca287 https://doi.org/10.1016/j.tetasy.2014.12.006 Zobrazit plný text záznamu Full Text from ScienceDirect