(2 S,3' S,3a' R,5' R,7a' R)-5'-[(E)-5-(Furan-3-yl)-2-methyl-pent-1-en-1-yl]-3-hy-droxy-3',4,7'-trimethyl-1',2',3',3a',5',7a'-hexa-hydro-5 H-spiro-[furan-2,4'-inden]-5-one

Thomas Majer; Dieter Schollmeyer; Pierre Koch; Harald Gross

doi:10.1107/S2414314620015783

(2 S,3' S,3a' R,5' R,7a' R)-5'-[(E)-5-(Furan-3-yl)-2-methyl-pent-1-en-1-yl]-3-hy-droxy-3',4,7'-trimethyl-1',2',3',3a',5',7a'-hexa-hydro-5 H-spiro-[furan-2,4'-inden]-5-one

IUCrdata. 2020 Dec 11;5(Pt 12):x201578. doi: 10.1107/S2414314620015783. eCollection 2020 Dec.

Authors

Thomas Majer¹, Dieter Schollmeyer², Pierre Koch³, Harald Gross¹

Affiliations

¹ Institute of Pharmaceutical Sciences, Department of Pharmaceutical Biology, Eberhard Karls University Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany.
² Department of Organic Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10-14, 55099 Mainz, Germany.
³ Institute of Pharmaceutical Sciences, Department of Pharmaceutical and Medicinal Chemistry, Eberhard Karls University Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany.

Abstract

The title compound, ircinianin, C₂₅H₃₂O₄, belongs to the sesterterpene tetronic acid compound family and was isolated from the marine sponge Ircinia wistarii. These chemical scaffolds are pharmacologically relevant, since they represent a new class of glycine receptor modulators. The furan ring makes a dihedral angle of 35.14 (12)° to the 4-hy-droxy-3-methyl-furan-2(5H)-one ring. The crystal packing is characterized by inter-molecular O-H⋯O hydrogen bonds, which generate [010] chains.

Keywords: crystal structure; ircinianin; natural product.