Preliminary studies on the incorporation of sugars into naphthoquinones: synthesis of (1R,2S,3S,4R,4aS,11bS)-2-(benzyloxy)-1,2,3,4,4a,5-hexahydro-1,3,4-trihydroxy-11bH-benzo[b]carbazole-6,11-dione

Autor:	Ramón J. Estévez, Juan C. Estévez, José C. Barcia, José M. Otero
Rok vydání:	2005
Předmět:	Nitroaldol reaction Carbazole Stereochemistry Organic Chemistry Enantioselective synthesis Total synthesis Catalysis Inorganic Chemistry chemistry.chemical_compound chemistry Intramolecular force Michael reaction Stereoselectivity Physical and Theoretical Chemistry
Zdroj:	Tetrahedron: Asymmetry. 16:11-14
ISSN:	0957-4166
Popis:	The first total synthesis of (1 R ,2 S ,3 S ,4 R ,4a S ,11b S )-2-(benzyloxy)-1,2,3,4,4a,5-hexahydro-1,3,4-trihydroxy-11b H -benzo[ b ]carbazole-6,11-dione from D -glucose is described. The key steps of this synthesis are the stereoselective Michael addition of 2-lithium-1,4-dimethoxynaphthalene to 3- O -benzyl-5,6-dideoxy-1,2- O -isopropylidene-6-nitro-α- D - xilo hex-5-enefuranose followed by the enantioselective intramolecular Henry reaction of 3- O -benzyl-5,6-dideoxy-5- C -(1,4-dimethoxynaphthalene-2-yl)-6-nitro-β- l -idofuranose to the key (1 R ,2 S ,3 S ,4 R ,5 S ,6 S )-3-(benzyloxy)-5-(1,4-dimethoxynaphthalene-2-yl)-1,2,4-trihydroxy-6-nitrocyclohexane.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::8b53add1d52b8933fa9994f6a0a1b8f6 https://doi.org/10.1016/j.tetasy.2004.11.045 Zobrazit plný text záznamu Full Text from ScienceDirect