Synthesis of functionalised cyclopentenones via rearrangement of pyranones

…, S Cheung, LM Frost, S Khan, G Pairaudeau

Index: Caddick, Stephen; Cheung, Steven; Frost, Lisa M.; Khan, Safraz; Pairaudeau, Garry Tetrahedron Letters, 2000 , vol. 41, # 35 p. 6879 - 6882

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Citation Number: 12

Abstract

During our investigation into the dienediyne anticancer antibiotics 1 we required a practical synthetic approach to functionalised cyclopentenone derivatives. We were particularly attracted to a seminal report which showed the isomerisation reaction of a pyranone to a dihydroxylated cyclopentenone derivative. 2 We were able to devise a modified procedure, which could be carried out on preparative scale (ca. 30 g) without the requirement of metal catalysts using only an amine base. 3 In ...