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- W1991301905 abstract "Starting from d-glucose, a novel sequence of the syntheses leading to (3S,5S,6S)-6-ethyl-3,5-dimethyltetrahydro-2H-pyran-2-one (4) is described. Key steps are the hydrogenation of 3,5,6-trideoxy-1,2-O-isopropylidene-3-C-methyl-α- d-glycero-hex-3,5-dienose leading to 3,5,6-trideoxy-1,2-O-isopropylidene-3-C- methyl-β-l-lyxo-hexofuranose, and the base-catalyzed cyclisation and isomerisation of methyl (2RS,4S,5S)-5-hydroxy-2,4-dimethylheptanoate into 4. Compound 4 can be converted by a known procedure into serricornin. Ausgehend von d-Glucose wird eine neue Synthese von (3S,5S,6S)-6-Ethyl- 3,5-dimethyltetrahydro-2H-pyran-2-on (4) beschrieben. Hydrierung der 3,5,6-Tridesoxy- 1,2-O-isopropyliden-3-C-methyl-α-d-glycero-hex-3-dienose zur 3,5,6-Trideoxy- 1,2-O-isopropyliden-3-C-methyl-β-l-lyxo-hexofuranose und basenkatalysierte Cyclisierung und Isomerisierung zum Lacton 4 sind Schlüsselschritte der Synthese. Verbindung 4 kann nach einem bekannten Verfahren in Serricornin umgewandelt werden." @default.
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- W1991301905 date "1988-03-01" @default.
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- W1991301905 title "Eine kurze synthese von serricornin, (4S,6S,7S)-4,6-dimethyl- 7-hydroxy-3-nonanon, dem sexualpheromon des tabakkäfers Lasioderma serricorne F., aus d-glucose" @default.
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- W1991301905 doi "https://doi.org/10.1016/0008-6215(88)85103-6" @default.
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