Stereoselective Synthesis of Bishomo-inositols as Glycosidase Inhibitors

For the synthesis of various bishomo-inositol derivatives, 1,3,3a,7a-tetrahydro-2-benzofuran was used as the key compound. For further functionalization of the diene unit, the diene was subjected to photooxygenation, epoxidation, and cis-hydroxylation reactions. The endoperoxide linkage was cleaved...

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Veröffentlicht in:	Journal of organic chemistry 2009-01, Vol.74 (1), p.88-95
Hauptverfasser:	Baran, Arif, Balci, Metin
Format:	Artikel
Sprache:	eng
Schlagworte:	Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Chemistry Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacology Exact sciences and technology Glycoside Hydrolases - antagonists & inhibitors Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Inositol - analogs & derivatives Inositol - chemical synthesis Inositol - chemistry Inositol - pharmacology Kinetics Molecular Conformation Organic chemistry Preparations and properties Stereoisomerism
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Beschreibung
Zusammenfassung:	For the synthesis of various bishomo-inositol derivatives, 1,3,3a,7a-tetrahydro-2-benzofuran was used as the key compound. For further functionalization of the diene unit, the diene was subjected to photooxygenation, epoxidation, and cis-hydroxylation reactions. The endoperoxide linkage was cleaved by thiourea. The remaining double bond was subjected to epoxidation and cis-hydroxylation reactions. The epoxide rings and tetrahydrofuran rings formed were opened by acid-catalyzed reaction with sulfamic acid. The combination of these reactions resulted in the formation of various new inositol derivatives such as bishomo-chiro-inositol, bishomo-myo-inositol, and two isomeric bishomo-allo-inositols.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo801344f