title: RDC-based determination of the relative configuration of the fungicidal cyclopentenone 4,6-diacetylhygrophorone A12..
abstract: The hygrophorones, a class of cyclopentenones isolated from fruiting bodies of the genus Hygrophorus (basidiomycetes), show promising antifungal activity. While the constitution of 4,6-diacetylhygrophorone A(12) (3) and the relative configuration of the stereogenic centers in the cyclopentenone ring were elucidated using standard NMR and MS techniques, the relative configuration of the exocyclic stereogenic center could not be assigned. By introducing a sample of 3 into an alignment medium and measuring anisotropic NMR parameters, namely, residual dipolar couplings, we were able to unambiguously determine the relative configuration of all three stereogenic centers in 4,6-diacetylhygrophorone A(12) simultaneously by fitting several structure proposals to the experimental data.
authors: Clemens Schöpf Institute for Organic Chemistry and Biochemistry, Technische Universität Darmstadt, Petersenstraße 22, Darmstadt, Germany.
authors: Volker
authors: V
authors: Schmidts
authors: Maic
authors: M
authors: Fredersdorf
authors: Tilo
authors: T
authors: Lübken
authors: Andrea
authors: A
authors: Porzel
authors: Norbert
authors: N
authors: Arnold
authors: Ludger
authors: L
authors: Wessjohann
authors: Christina M
authors: CM
authors: Thiele
mesh_terms: D001487:Basidiomycota / Q000737:chemistry*; D003517:Cyclopentanes / Q000737:chemistry / Q000145:classification / Q000302:isolation & purification* / Q000494:pharmacology*; D005659:Fungicides, Industrial / Q000737:chemistry / Q000145:classification / Q000302:isolation & purification* / Q000494:pharmacology*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular
chemical_list: C582889:4,6-diacetylhygrophorone A12; D003517:Cyclopentanes; D005659:Fungicides, Industrial; C013905:cyclopentenone