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.

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.

The first representatives of a new class of eremophilone dimers have been isolated from the wood oil of Eremophila mitchelli and shown by a combination of spectroscopic and X-ray techniques to possess the unusual 1-(8',8'a-dimethylperhydronaphthalen-2'-yl)-1,4,5,10a-tetramethylperhydroanthracene carbon skeleton. These two natural products are the first C30 compounds to be isolated from any member of the genus Eremophila.

An unambiguous synthesis of the phenyl analogue of freelingyne from the Wittig reaction of a C5 butenolide phosphorane with (E)-2-methyl-5-phenylpent-2-en-4-yn-l-a1 has confirmed that freelingyne is (2Z,4Z,6E)-9-(3'-furyl)-2,6-dimethylnona-2,4,6-trien-8-yn-4-olide (1). A similar stereo-selective synthesis has shown that the naturally occurring dihydrofreelingyne is (2Z,4Z,6E,8E)- 9-(3'-furyl)-2,6-dimethylnona-2,4,6,8-tetraen-4-olide (2).

Die Reformatsky‐Reaktion des Furylbrompropins (I) mit dem (4E)‐Enollacton (II) ergibt das Hydroxynonadienolid (IIIa), das mit Acetylchlorid in N,N‐Dimethyl‐anilin/CHC13 (O°) zu (IIIb) acetyliert wird.