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Radical Cyclization in Heterocycle Synthesis. Part 9: A Novel Synthesis of Aminocyclitols and Related Compounds via Stannyl Radical Cyclization of Oxime Ethers Derived from Sugars

✍ Scribed by Toshiko Kiguchi; Kazumi Tajiri; Ichiya Ninomiya; Takeaki Naito

Book ID: 104202858
Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 266 KB
Volume: 56
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(00)00545-7

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✦ Synopsis

AbstractÐStannyl radical addition±cyclization of oxime ethers derived from d-glucose, d-galactose, and d-xylose proceeded smoothly to afford alkoxyamino alcohols which were effectively converted into two types of glycosidase inhibitors or its candidates such as aminocyclitols, 1-deoxynojirimycin, and 1-deoxygalactostatin via reductive ring-expansion of trans alkoxyamino alcohols.

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