Journal of the Chemical Society. Perkin transactions I p. 95 - 102 (1992)
Update date:2022-08-16
Topics:
Carling, Robert W.
Clark, J. Stephen
Holmes, Andrew B.
Sartor, Dirk
Synthesis of the cis- and trans-2,8-disubstituted oxocane derivatives 2 and 3 (carrying the unusual γ,δ-diketohexanecarboxylic acid side chain) by ozonolysis of the alkynes 14 and 18 (prepared respectively from the alcohols 11 and 15) demonstrated unequivolally that neither of these compounds nor their hydroxy-γ-lactone ring (lactol) tautomeres 1 correspond to the naturally occurring fungal self germination inhibitor gloeosporone.A study of 4,5-dioxohexanoic itself 9 revealed a remarkably low tendency to exist as its hydroxy-γ-lactone (lactol) tautomer 10.
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