Synthesis of 5-aza-analogues of angucyclines: manipulation of the 2-deoxy-C-glycoside subunit

Autor:	Sylvain Collet, Michel Evain, Eun-Ang Raiber, André Guingant, Gilles Dujardin, Nguyen Quang Vu
Rok vydání:	2005
Předmět:	C glycosides Residue (chemistry) Stereochemistry Chemistry Protein subunit Organic Chemistry Drug Discovery chemistry.chemical_element Organic chemistry Sugar Biochemistry Carbon Angucyclinone
Zdroj:	Tetrahedron Letters. 46:7669-7673
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2005.09.053
Popis:	Based on a heterocyclic Diels–Alder strategy, a concise synthesis of 5-aza-analogues of angucyclines bearing a 2-deoxy-C-glycoside subunit is reported. Starting from a common intermediate, a peracetylated D-2-deoxyglucose could be linked to carbons C9 or C10 of the tetracyclic framework. Further manipulations of the sugar residue allowed the installation of bromo and azido substituents at carbon C6′.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::9c87575e54bccf867676bbf9f7b51537 https://doi.org/10.1016/j.tetlet.2005.09.053 Zobrazit plný text záznamu Full Text from ScienceDirect