The Synthesis of 5-Hydroxy-3-methylnaphtho [2, 3-c] furan-4, 9-dione and 5, 8-Dihydroxy-1-methylnaphtho [2, 3-c] furan-4, 9-dione

MJ Piggott, D Wege

Index: Piggott, Matthew J.; Wege, Dieter Australian Journal of Chemistry, 2003 , vol. 56, # 7 p. 691 - 702

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Citation Number: 13

Abstract

Abstract 5-Hydroxy-3-methylnaphtho [2, 3-c] furan-4, 9-dione (1), a metabolite isolated from Aloe ferox and Bulbine capitata, has been synthesized by a sequence involving an annulation reaction between the anion of 4-methoxy-3-oxo-1, 3-dihydroisobenzofuran-1- carbonitrile (8) and (E)-pent-3-en-2-one, followed by subsequent construction of the furan ring through allylic bromination, hydrolysis, and dehydration as the key steps. The ...