Several enol-lactones have been synthesized successfully from the reaction of stabilized phosphoranes with various substituted succinic and maleic anhydrides. Nuclear magnetic resonance spectroscopy and chemical interconversions have been used to establish the stereochemistry of the products. Where both (E) and (Z) isomers were formed the mixture could be separated readily.

Acetylation of the tertiary alcohol prepared from the Reformatsky reaction of 1-bromo-3-(3'-furyl)prop-2-yne with (2Z,4E)-2-methyl-6-oxohepta-2,4-dien-4-olide gave the acetate. Flash vacuum pyrolysis of the tertiary acetate gave a mixture of predominantly two isomers, one of which was freelingyne, (2Z,4Z,6E)-9-(3'-furyl)-2,6-dimethylnona-2,4,6-trien-8-yn-4-oide (1). The synthesis of the phenyl analogues is also described.

8α-Hydroxy-7α(H)-eremophila-1,ll-dien-9-one and 8α-hydroxy-7α(H)-eremophila-l0,ll-dien-9-one have been isolated from the wood oil of Eremophila mitchelli and their structure shown to be (I) and (11) respectively.

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Treatment of freelingyne (1) with sodium hydroxide in aqueous methanol gives the rearranged acid (2a).