The crystal structure of (S)-( - )-6-Bromo-5,7-dihydroxy-8-methyl-2-phenyl-2,3-dihydro-4H-1-benzopyran-4-one [( - )-6-bromocryptostrobin] and a 13C N.M.R. study of (±)-cryptostrobin and related substances. Revision of the structures of the natural products (±)-lawinal, unonal, 7-O-methylunonal and isounonal

Australian Journal of Chemistry
1982.0

Abstract

<jats:p>The crystal structure of (S)-(-)-6-bromo-5,7-dihydroxy-8-methyl-2-phenyl-2,3-dihydro-4H-1-benzopyran-4-one [(–)-6-bromocryptostrobin] (11) has been determined by X-ray diffraction from diffractometer data at 295 K and refined by block diagonal least squares to a residual of 0.050 (810 'observed' reflections). Crystals of (11) are tetragonal, P43212, a 7.849(4), c 46.83(2) �, Z 8. The crystallographic data are consistent with the S configuration previously proposed for (–)-cryptostrobin (10). The 13C n.m.r, spectra of (�)-cryptostrobin and(�)-strobopinin also lead to the structures (1) and (6), respectively. This work has enabled the structures proposed for the natural products (�)-lawinal, unonal, 7-O-methylunonal and isounonal to be revised to (8), (14), (15) and (12), respectively.

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