Intramolecular cyclization reactions of 5-halo-and 5-nitro-substituted furans

KR Crawford, SK Bur, CS Straub, A Padwa

Index: Crawford, Kenneth R.; Bur, Scott K.; Straub, Christopher S.; Padwa, Albert Organic Letters, 2003 , vol. 5, # 18 p. 3337 - 3340

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Citation Number: 41

Abstract

Intramolecular cyclization reactions of 5-halo-and 5-nitro-substituted furanylamides were examined. The 2-alkoxy-5-bromofuran derivative 2 produced the rearranged dihydroquinone 6 (36%), a product from the rearrangement of the intermediate oxabicycle 3. The 5-halo substituted furoyl amide 18 was converted to the polyfunctional oxabicycle 20 in 82% yield and at a much faster rate than the unsubstituted furanyl system 17. The 5-nitro- ...