Partial Reduction of Annulated Heterocycles as a General Route to Medium Rings Containing Oxygen and Nitrogen

TJ Donohoe, A Raoof, ID Linney, M Helliwell

Index: Donohoe; Raoof; Linney; Helliwell Organic letters, 2001 , vol. 3, # 6 p. 861 - 864

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Citation Number: 21

Abstract

The preparation of annulated furans and pyrroles is described as part of a general strategy for the synthesis of medium ring heterocycles. After Birch reduction, the corresponding dihydro compounds were oxidatively cleaved to produce medium ring ethers and amines in an efficient manner. This methodology was successfully applied to the formation of eight-and nine-membered cyclic ethers and nine-membered cyclic amines. Attaching a chiral ...