The conversion of ethyl dienol ether and dienyl pivalate derivatives of hagemann’s ester into bicyclic enones

Murray V. Baker, Christine Ghitgas, Robert J. Dancer, Richard K. Haynes, Gloria V. Sherwood

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

The cyclization of compounds obtained from ethyl dienol ether and dienyl pivalate derivatives of Hagemann’s ester has been examined. The carbanions of methyl phenyl sulfone and methyl phenyl sulfoxide react with the methylated dienol ether (4) to give the β-keto sulfone (8) and sulfoxide (9), the former of which was converted into the oxabicyclo[4.3.0]non-l-en-3-one (16). The iodide (17) with potassium t-butoxide in t-butyl alcohol gave the octahydronaphthalenone (18). With lithium ethoxide in tetrahydrofuran the octahydronaphthalenedione (22) was obtained from the dienyl pivalate (24). Both reactions involve the generation and intramolecular cyclization of a dienolate produced by cleavage of the pivaloyl group in each of (17) and (24). The scope and limitations of these reactions are briefly discussed.

Original languageEnglish
Pages (from-to)1331-1340
Number of pages10
JournalAustralian Journal of Chemistry
Volume40
Issue number8
DOIs
Publication statusPublished - 1987

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