Stereocontrolled spirocyclization of exo-glucal derivatives for stereodivergent synthesis of spiro[5.5]ketals

Autor:	Takashi Yamanoi, Yoshiki Oda, Akihiro Yoshida, Sho Matsuda, Mikio Watanabe, Junki Nakagawa
Rok vydání:	2014
Předmět:	Glycosylation Stereochemistry Spiro compound Organic Chemistry Stereoselective synthesis Biochemistry Lewis acid chemistry.chemical_compound chemistry Cyclization Intramolecular force Drug Discovery Side chain Stereoselectivity Glucal
Zdroj:	Tetrahedron Letters. 55:6394-6398
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2014.09.095
Popis:	This Letter describes a stereoselective synthetic approach to spiro[5.5]ketals from the exo-glucals, constructed from 1-(4-hydroxyalkylidene)-1,5-anhydro- d -glucitol, by spirocyclization based on intramolecular α- and β-selective glycosylation. Stereodivergent synthesis of both α- and β-glucoside of spiro[5.5]ketals was attained by combination of chiral d -glucopyranose environment and C-4′ chiral center on the side chain.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::e2a26e87e393184395ea1cb9a2ed2a3d https://doi.org/10.1016/j.tetlet.2014.09.095 Zobrazit plný text záznamu Full Text from ScienceDirect