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Formal synthesis of (−)-stemoamide using a useful epimerization at C-8

✍ Scribed by Subhash P. Chavan; Kishor R. Harale; Vedavati G. Puranik; Rupesh L. Gawade

Book ID
113930706
Publisher
Elsevier Science
Year
2012
Tongue
French
Weight
673 KB
Volume
53
Category
Article
ISSN
0040-4039

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✍ Mukund K Gurjar; Dandepally Srinivasa Reddy 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 172 KB

A synthesis of stemoamide has been achieved from D-glucose. The stereocontrolled allylation under Barbier reaction conditions led to the installation of the 2-pyrrolidinone ring at C-3 followed by a ring-closing metathesis approach to construct the azepine ring system.