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- W2078359768 endingPage "2052" @default.
- W2078359768 startingPage "2009" @default.
- W2078359768 abstract "Starting from the dianhydro-epi-inositol 10 (available ultimately from benzene) an expedient total synthesis of enantiomerically pure (+)/(−)-de-O-methylfortamines (derivatives) has been developed. Key steps are the regiospecific epoxide openings which occur intramolecularly in the diepoxybis(urethane) 11 and intermolecularly by (+)-1-phenylthylamine in the epoxyurethanes rac-13. The diastereomeric adducts (30, 32) are quantitatively separated by crystallization/chromatogrphy. Following hydrogenation, natural and nonnatural cis-1,4-inosadiamines are obtained optically pure [e.g. fortamine (−)-1, ent-fortamine (+)-1, 3-O-demethylfortamine (−)-38, ent-3-O-demethylfortamine (+)-38]. This approach, which was optimized by numerous model reactions, allows wide chemical modifications and leads among others to 3-O-demethylfortamine and ent-fortamine derivatives in which only the (6)4-OH-group, the one to be glycosidated, remains unprotected. Aminoglycosid-Antibiotika – Fortamin-Aglyca Totalsynthese, Racemattrennung, chemischen Modifizierungen Ausgehend von Dianhydro-epi-inosit 10 (letztlich erhältlich aus Benzol) wurde eine leistungsfähige Synthese für enantiomerenreine (+)/(−)-Des-O-methylfortamine (Derivate) entwickelt. Zentrale Schritte sind die regiospezifischen Epoxidöffnungen, intramolekular beim Diepoxybis(urethan) 11 und intermolekular mit (+)-1-Phenylethylamin bei den Epoxyurethanen rac-13. Die diastereomeren Addukte (30, 32) können verlustfrei durch Kristallisation/Chromatographie getrennt werden. Nach hydrierender Spaltung werden natürliche und nicht natürliche cis-1,4-Inosadiamine enantiomerenrein erhalten [z. B. Fortamin (−)-1, ent-Fortamin (+)-1, 3-O-Desmethylfortamin (−)-38, ent-3-O-Desmethylfortamin (+)-380]. Der in zahlreichen Modellreaktionen optimierte Syntheseweg erlaubt breite chemische Modifizerungen und führt u.a.zu 3-O-Desmethylfortamin- und ent-Fortamin-Derivaten, in denen nur die zur Glycosidierung gebrauchte (6)4-OH-Gruppe ungeschützt bleibt." @default.
- W2078359768 created "2016-06-24" @default.
- W2078359768 creator A5030787548 @default.
- W2078359768 creator A5038157783 @default.
- W2078359768 creator A5056529947 @default.
- W2078359768 creator A5070987986 @default.
- W2078359768 date "1986-12-12" @default.
- W2078359768 modified "2023-10-17" @default.
- W2078359768 title "Aminoglycoside Antibiotics – Fortamine Aglyca Total Synthesis, Optical Resolution, Chemical Modifications" @default.
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