Freelingnite, a new furanosesquiterpene from eremophila freelingii

✍ Scribed by David W. Knight; Gerald Pattenden

• Book ID: 104213588
• Publisher: Elsevier Science
• Year: 1975
• Tongue: French
• Weight: 99 KB
• Volume: 16
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)72072-7

✦ Synopsis

Reoeived in UK 10 lMeu8ry 19758 aooepted for publication 19 Sbbruary 1975) Freelingyne (3) from Eremophila freelingii was the first acetylenic terpenoid -_ to be isolated from Nature.1 Its biosynthesis poses several interesting problems. Here we report the presence of a new furanosesquiterpene, freelingnite, in E. freelingii whose structure (1) has a direct bearing on considerations of the biosynthesis of (3). Freelingnite represents the first example of a furanosesquiterpene containing a 4-alkylbut-2-enolide moiety. Chromatography of the acetone extract of the ground twig-wood of E. freelingii (silica gel -chloroform, then 1:l pentane-ether) gave freelingnite (-.O.Ol%) as an oil, [aID 25 + ll.SO(dioxan,c 1.3). The infrared spectrum showed the presence-of an a,b-unsaturated v-lactone (wmax 1755t%t),