(2S,3′S,3a'R,5′R,7a'R)-5′-[(E)-5-(Furan-3-yl)-2-methylpent-1-en-1-yl]-3-hydroxy-3′,4,7′-trimethyl-1′,2′,3′,3a',5′,7a'-hexahydro-5H-spiro[furan-2,4′-inden]-5-one

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-hydroxy-3-methylfuran-2(5H)-one ring. The crystal packing is characterized by intermolecular O—H...O hydrogen bonds, which generate [010] chains.

One-pot synthesis of cyclic β-dicarbonyl compounds as synthons for 11-deoxyprostanoids

One-pot synthesis of cyclic β-dicarbonyl synthons for 11-deoxyprostanoids has been developed on the basis of cyclopentane-1,3-dione and 5-phenyl tetronic acid. The obtained 2-alkyl(arylalkyl)-substituted cyclopentane-1,3-diones have been transformed into cyclopentenone precursors of 11-deoxy-PGE 1 and 11-deoxy-PGE 2 analogues.