Synthesis of a New Spirolactone: 7,10-Dimethoxy-1-oxaspiro[4,5]deca-6,9-diene-2,8-dione

Guy L. Plourde, Mark D. Fairchild, Gurkaran S. Sarohia


The title compound was synthesized in 36 % yield by oxidative spiroannulation of the corresponding 2,4,5-trisubstituted phenol. Interestingly, this phenol was prepared in 57 % yield from another spirocompound, namely 7-methoxy-1-oxaspiro[4,5]deca-6,9-diene-2,8-dione. We have speculated that the formation of the phenol was due to a series of reactions involving a conjugate addition of methanol to the original spirolactone followed by aromatization and lactone hydrolysis.

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International Journal of Chemistry   ISSN 1916-9698 (Print)   ISSN 1916-9701 (Online)

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