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The First Synthesis of Herbicidin B. Stereoselective Construction of the Tricyclic Undecose Moiety by a Conformational Restriction Strategy Using Steric Repulsion between Adjacent Bulky Silyl Protecting Groups on a Pyranose Ring †

✍ Scribed by Ichikawa, Satoshi; Shuto, Satoshi; Matsuda, Akira


Book ID
121252738
Publisher
American Chemical Society
Year
1999
Tongue
English
Weight
469 KB
Volume
121
Category
Article
ISSN
0002-7863

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Synthesis of C-glycosides via radical cy
✍ Yumi Yahiro; Satoshi Ichikawa; Satoshi Shuto; Akira Matsuda 📂 Article 📅 1999 🏛 Elsevier Science 🌐 French ⚖ 288 KB

A stereoselective method for introducing a C2-unit at the 1 or-and 1 I~-postions of D-glucose and D-mannose, respectively, via a radical cyclization reaction with vinylsilyl group as a temporary connecting tether, was developed. The radical cyclization of D-glucose substrates was effectively facilit