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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

Piggott, Matthew; Wege, Dieter


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 formation of several unusual products observed in annulation reactions between...[Show more]

CollectionsANU Research Publications
Date published: 2003
Type: Journal article
Source: Australian Journal of Chemistry


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