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Total Synthesis of cis - and trans -3-Hydroxy- d -proline and (+)-Detoxinine †

✍ Scribed by Mulzer, Johann; Meier, Andreas; Buschmann, Jürgen; Luger, Peter


Book ID
127024184
Publisher
American Chemical Society
Year
1996
Tongue
English
Weight
321 KB
Volume
61
Category
Article
ISSN
0022-3263

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Total synthesis of natural cis-3-hydroxy
✍ Navnath B. Kalamkar; Vijay M. Kasture; Dilip D. Dhavale 📂 Article 📅 2010 🏛 Elsevier Science 🌐 French ⚖ 265 KB

Synthesis of cis-3-hydroxy-L-proline from D-glucose is reported. The methodology involves conversion of D-glucose into N-benzyloxycarbonyl-c-alkenyl amine which on 5-endo-trig-aminomercuration gave the pyrrolidine ring skeleton with sugar appendage in 25% yield. Alternatively, N-benzyloxycarbonyl-c-