Enantioselective synthesis of antibiotic (+)-rancinamycin III derivative and two protected carbasugars of the α-d-talo-series from furan

Autor:	Fátima Iradier, Odón Arjona, Rocio Medel, Joaquín Plumet
Rok vydání:	1999
Předmět:	chemistry.chemical_classification Diene Stereochemistry Organic Chemistry Diol Enantioselective synthesis Carbasugars Alkyne Alcohol Carbonyl group Catalysis Inorganic Chemistry chemistry.chemical_compound chemistry Furan Physical and Theoretical Chemistry
Zdroj:	Tetrahedron: Asymmetry. 10:3431-3442
ISSN:	0957-4166
Popis:	The synthesis of (+)- 1 , a carbasugar related to rancinamycin III, has been achieved from diene (+)- 3 in two steps using as the key step the transformation of alkyne (−)- 2 , obtained by resolution of alcohol 6 , into diene (+)- 3 by treatment with Na/MeOH. Moreover, reduction of the carbonyl group in (+)- 1 affords diol (+)- 19 , in which different protection strategies of the hydroxy groups allows one to obtain, selectively, protected derivatives of α- d -carbatalopyranose (+)- 4a and its 6-desoxy derivative (+)- 4b to be obtained selectively.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::76481425fb830127d510fca47b8cb13e https://doi.org/10.1016/s0957-4166(99)00358-4 Zobrazit plný text záznamu Full Text from ScienceDirect