title: Isogermacrene A, a proposed intermediate in sesquiterpene biosynthesis.
abstract: In the essential oil of the liverwort Saccogyna viticulosa, collected on the island of Madeira, the new sesquiterpene hydrocarbons isogermacrene A (5) and its Cope rearrangement product iso-beta-elemene (6) were identified. 5 is proposed to act as the biogenetic precursor of several new sesquiterpenes identified in the volatiles of S. viticulosa. These include iso-alpha-humulene, alpha-gorgonene, gorgona-1,4(15), 11-triene and gorgon- 11-en-4-ol. In addition, the Cope product of zierene, isozierene, allo-aromadendra-4(15),10(14)-diene, aromadendra-4(15),10(14)-dien-1-ol and a prenylguaiane diterpene alcohol, named viticulol, were identified as new natural products.
authors.affiliation: Institut für Organische Chemie, Universität Hamburg, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany. thomas_hackl@public.uni-hamburg.de
authors.forename: Thomas
authors.initials: T
authors.lastname: Hackl
authors.forename: Wilfried A
authors.initials: WA
authors.lastname: König
authors.forename: Hermann
authors.initials: H
authors.lastname: Muhle
mesh_terms: D008401:Gas Chromatography-Mass Spectrometry; D035926:Hepatophyta / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D009822:Oils, Volatile / Q000737:chemistry* / Q000302:isolation & purification; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification; D045788:Sesquiterpenes, Germacrane / Q000737:chemistry*
chemical_list: C495686:Isogermacrene A; D009822:Oils, Volatile; D012717:Sesquiterpenes; D045788:Sesquiterpenes, Germacrane