The fungal metabolite austdiol.
The title compound, (7R,8S)-7,8-dihydroxy-3,7-dimethyl-6-oxo-7,8-dihydro-6H-isochromene-5-carbaldehyde, C(12)H(12)O(5), is a trans-vicinal diol. Of the two fused rings, which lie approximately in the same plane, the pyran ring is almost perfectly planar, while the cyclohexenone ring adopts a slightly distorted half-chair conformation. The crystal packing is dictated by two strong intermolecular O-H.O interactions, one involving hydroxy and keto groups, the other involving two hydroxy groups. Molecules are linked together through twofold axes, forming zigzag ribbons extended along the a axis.
Lo Presti
Leonardo
L
Dipartimento di Chimica Fisica ed Elettrochimica, Università degli Studi di Milano, Via C. Golgi 19, I-20133 Milano, Italy.
Soave
Raffaella
R
Destro
Riccardo
R
D000447:Aldehydes / Q000737:chemistry*; D001230:Aspergillus / Q000737:chemistry; D001578:Benzopyrans / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003512:Cyclohexanones / Q000737:chemistry; D006860:Hydrogen Bonding; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D011714:Pyrans / Q000737:chemistry
D000447:Aldehydes; D001578:Benzopyrans; D003512:Cyclohexanones; D011714:Pyrans; C474729:austdiol