Synthese von Azaprotoanemoninen

Abstract

H, C'\O COOH CH3 CH3 111 a, b, c, d I V a, b, c, d Unter denselben Reaktionsbedingungen erhielten wir aus : a) Aceton und Glyoxylsaure 45% tram-4-0~0-2-pentensaure (IIIa) [7], 1) Betr. Aufbau von Azaprotoanemonin-Derivaten, welche sowohl an der exocyclischen Methylengruppe, als auch am Stickstoff alkyliert sind, siehe WALTON [4]. 2) Wahrend der Abfassung dieser Arbeit haben PLIENINGER & LERCH [S] die Synthesen von 3,4-Diniethylazaprotoanemonin (IId) und 3-Methyl-4-ath yl-azaprotoanemonin ausgehend von den entsprechenden 3,4-Dialkylpyrrolonen veroffentlicht. Anm. b. d . Korr. (30.3.67) : Vgl. dazu die Arbeit uber Methylcn-pyrrolone von v. DOBENECK & SCHNIERLE [5a]. e) E n t h a t gemass NMR.-Spektrum ca. 15% Irans-4-0~0-2-pentensaure (IIIa). f) Die Titrationskurve zeigt keine Stufe. Der angegebene Wert entspricht dem pH-Wert nach MOSER (vgl. [6]) entnommen.Zugabe der theoretisch zur halben Neutralisation notigen Basenmenge.

Allylic Oxidations Catalyzed by Dirhodium Caprolactamate via Aqueous tert-Butyl Hydroperoxide: The Role of the tert-Butylperoxy Radical

“…After an additional 24 hrs, the solution was concentrated and purified by column chromatography to obtain analytically pure compounds whose spectral characteristics were identical to those previously reported: trans -3-nonen-2,5-dione ( 1 ),11 ethyl ( E )-4-oxo-2-decenoate ( 2 ) 42. ( E )-4-oxo-2-pentenamide ( 5 ),43 4-androsten-17β-3,6-dione ( 25 ),44 17β-acetoxyandrost-4-en-3,6-dione ( 26 ),45 4-androstene-3,6,17-trione ( 27 ),46 4-cholesten-3,6-dione (28) 47 and acids were purified by recrystallization in ethyl acetate and matched with those in the literature: ( E )-4-oxo-2-nonenoic acid ( 3 ),25a ( E )-4-oxo-2-pentenoic acid ( 4 ),48 2-cyclohexenone-1-carboxylic acid ( 7 ) 49. and fumaric acid monomethyl ester ( 8 ) 50…”

Extract of the mushroom Mycoleptodonoides aitchisonii induces a series of anti-oxidative and phase II detoxifying enzymes through activation of the transcription factor Nrf2

“…Thus,1,3,6,7,8,9,10, and 11 were identified as 4-acetyl-3-methyl-dihydro-furan-2-one (Forzato et al, 2005), 5-hydroxy-3,4,5-trimethyl-5-H-furan-2-one (Scheffold & Dubs, 1967), (E)-2-decenedioic acid (Noda, Umebayashi, Nakatani, Miyahara, & Ishiyama, 2005), 1-phenyl-pentane-1,3-diol (Giuseppe et al, 2001), 2-phenyl-pyran-4-one (Groundwater, Hibbs, Hoursthouse, & Nyerges, 1997), dihydro-4-phenyl-2(3H)-furanone (Bavin, Hansell, & Spicket, 1964), 2-phenyl-5,6-dihydro-c-pyrone (Satoh, Yamashiro, Nomura, & Nakata, 2008), and 2-(2-formylpyrrol-1-yl)-4-methylvaleric acid (Chan & Lee, 1983), respectively, by comparison with reported data. Compounds 1, 3, 7, 8, and 9 have never been reported as natural products.…”

Glutamine analogues containing a keto function – novel inhibitors of fungal glucosamine-6-phosphate synthase

“…All the other (E)-4-oxo-4-phenyl-2-butenoic acids 2 f -q and compounds where the phenyl ring was replaced by furyl 2 r, pyrrolyl 2 s or tert-butyl 2 t group were prepared by condensation of an appropriate methyl ketone with glyoxylic acid (Method B, Table I) [17,18]. The three acids 2 u-x were prepared via condensation of the appropriate aldehyde with propionlaldehyde diethyl acetal followed by oxidation and hydrolysis (Method C, Table I) [19].…”