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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 …

T Kiguchi, K Tajiri, I Ninomiya, T Naito

Index: Kiguchi, Toshiko; Tajiri, Kazumi; Ninomiya, Ichiya; Naito, Takeaki Tetrahedron, 2000 , vol. 56, # 32 p. 5819 - 5833

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Citation Number: 33

Abstract

Stannyl 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.