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Reactions of Nepenthone with Chromium(II) Reagents in Neutral Aqueous Medium

✍ Scribed by Károly Micskei; Julianna Gyarmati; Gábor Kovács; Sándor Makleit; Csaba Simon; Zoltán Szabó; János Marton; Sándor Hosztafi; Helmut Reinke; Hans-Joachim Drexler


Book ID
101278320
Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
162 KB
Volume
1999
Category
Article
ISSN
1434-193X

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✦ Synopsis


Morphine alkaloids / 6,14-Ethenomorphinans / Chromium(II) complex reagents / Organochromium(III) complex intermediates A synthetic method for the selective transformations of a reactions with classical reagents to result in 2b (20S). A new unexpected morphine derivative 3 was prepared by a ligand-selected morphine alkaloid in neutral aqueous medium is introduced. Full diastereoselectivity was achieved by the induced modification of the reaction which involves an unprecedented rearrangement. transformation of nepenthone ( ) with [Cr(ida)(H 2 O) 3 ] into 2a (20R) showing a complementary method as compared to the [a] Department of Inorganic and Analytical Chemistry, Lajos Kos-"biomimetic setup" using only additives to control the reac-


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✍ Gyöngyvér Kovács; Krisztina Tóth; Zoltán Dinya; László Somsák; Károly Micskei 📂 Article 📅 1999 🏛 Elsevier Science 🌐 French ⚖ 717 KB

Reactions of 2,3,4,6-tetra-O-acetyl-ct-D-glucopyranosyl bromide (3) with chromium(II)L complexes (L = EDTA, NTA` IDA, GLY, MAL) in neutral (5 < pH < 7) aqueous DMF gave 3,4,6-tri-O-acetyl-l,5anhydro-2-deoxy-D-arabino-hex-l-elfitol (13) in 70-90% yields and >95% purity. Complexes of Cr(lI) with L = E