Stereoselective Synthesis of Polyhydroxycycloheptanes and Their Phosphate Derivatives from 8-Oxabicyclo[3.2.1]octenes

Autor:	S. E. Sosonyuk, Nikolay S. Zefirov, Dmitry A. Khlevin, Marina V. Proskurnina
Rok vydání:	2013
Předmět:	chemistry.chemical_compound Chemistry Dihydroxylation Stereochemistry Organic Chemistry Enantioselective synthesis Carbasugars Stereoselectivity Physical and Theoretical Chemistry Ring (chemistry) Phosphate
Zdroj:	European Journal of Organic Chemistry. 2013:2381-2388
ISSN:	1434-193X
Popis:	The first directed synthesis of seven-membered mono- and tris-phosphates is described. The key steps involve a DIBAL-H/DIBAL-Cl-mediated ring opening of 8-oxabicyclo[3.2.1]octenes in the presence of [Ni(acac)2] and stereoselective syn-dihydroxylation with NMO and OsO4. An enantioselective approach to ring opening has been examined with chiral phosphane. The phosphorylation of mono- and triols followed by deprotection gave the corresponding phosphates in high yields with structures similar to those of known inhibitors of myo-inositol monophosphatase (IMPase) and myo-inositol tris-phosphate receptor ligands. The inhibitory activities of the monophosphates thus formed were evaluated against IMPase.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::8eb6bbbfdec01d31f85dfbdd23329c66 https://doi.org/10.1002/ejoc.201201426 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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