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(3S,11Z)-14,16-Dihy-droxy-3-methyl-3,4,5,6,9,10-hexa-hydro-1H-2-benz-oxacyclo-tetra-decine-1,7(8H)-dione (cis-zearalenone): a redetermination.

ABSTRACT: The title compound, also known as cis-zearalenone (cis-ZEN), C(18)H(22)O(5), has already been reported elsewhere [Griffin et al. (1981 ?). ACA Ser.29, 35], but no atomic coordinates are publicly available. The mol-ecule is of inter-est with respect to its toxicity. In the crystal, intra-molecular O-H?O hydrogen bonds stabilize the mol-ecular conformation, while inter-molecular O-H?O hydrogen bonds link the mol-ecules to form infinite chains along the [110] and [1-10] directions. The absolute configuration has been assigned by reference to an unchanging chiral centre in the synthetic procedure.

SUBMITTER: Koppen R

PROVIDER: S-EPMC3297891 | biostudies-other | 2012 Mar

REPOSITORIES: biostudies-other

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(3S,11Z)-14,16-Dihy-droxy-3-methyl-3,4,5,6,9,10-hexa-hydro-1H-2-benz-oxacyclo-tetra-decine-1,7(8H)-dione (cis-zearalenone): a redetermination.

Köppen Robert R Riedel Juliane J Emmerling Franziska F Koch Matthias M

Acta crystallographica. Section E, Structure reports online 20120224 Pt 3

The title compound, also known as cis-zearalenone (cis-ZEN), C(18)H(22)O(5), has already been reported elsewhere [Griffin et al. (1981 ▶). ACA Ser.29, 35], but no atomic coordinates are publicly available. The mol-ecule is of inter-est with respect to its toxicity. In the crystal, intra-molecular O-H⋯O hydrogen bonds stabilize the mol-ecular conformation, while inter-molecular O-H⋯O hydrogen bonds link the mol-ecules to form infinite chains along the [110] and [1-10] directions. The absolute con ...[more]

PMID: 22412694

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(3S)-14,16-Dihy-droxy-3-methyl-3,4,5,6,9,10,11,12-octa-hydro-1H-2-benzoxacyclo-tetra-decine-1,7(8H)-dione (zearalanone) monohydrate.

Project description:The absolute configuration of the title compound, C(18)H(24)O(5)·H(2)O, was not been determined by anomalous-dispersion effects, but has been assigned by reference to an unchanging chiral centre in the synthetic procedure. Intra-molecular O-H⋯O hydrogen bonds stabilize the mol-ecular conformation. In the crystal, O-H⋯O hydrogen bonds link the main mol-ecules and the water mol-ecules, forming an infinite three-dimensional network.

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Project description:The absolute configuration of the title compound, C(10)H(17)NO(3)·H(2)O, was assigned from the synthesis. In the mol-ecular structure, the central six-membered ring of the indolizine moiety adopts a chair conformation, with two atoms displaced by -0.578?(2) and 0.651?(1)?Å from the plane of the other four atoms [maximum deviation 0.019?(2)?Å] The conformation of the fused oxopyrrolidine ring is close to that of a flat envelope, with the flap atom displaced by 0.294?(1)?Å from the plane through the remaining four atoms. In the crystal, one of the hy-droxy groups is hydrogen-bonded to two water mol-ecules, while the other hy-droxy group exhibits an inter-molecular hydrogen bond to the carbonyl O atom, resulting in a chain parallel to the b axis.

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(1S,2E,6R,7aR)-2-Benzyl-idene-1,6-dihy-droxy-2,3,5,6,7,7a-hexa-hydro-1H-pyrrolizin-3-one.

Project description:In the title compound, C(14)H(15)NO(3), the conformation of the double bond was determined to be E, confirming the result obtained from two-dimensional NMR data. The five-membered rings of the pyrrolizine unit exhibit C-envelope conformations, with C atoms displaced from the mean planes formed by the remaining rings atoms by 0.1468 (15) and 0.5405 (17) Å. The mean planes of these rings (through all ring atoms) have a dihedral angle of 49.03 (10)°. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds. The absolute configuration of the mol-ecule was established, as judged by the, as judged by the obtained values for the Hooft and Flack parameters.

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11α,15α-Dihy-droxy-androst-4-ene-3,17-dione.

Project description:The title compound, C(19)H(26)O(4), was biotransformed from androstenedione. In the crystal, inter-molecular O-H⋯O hydrogen bonds link molecules into a corrugated sheet, which lies parallel to the ab plane. Ring A has a slightly distorted half-chair conformation, rings B and C adopt chair conformations, while the cyclo-pentane ring D adopts a 14α-envelope conformation.

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(1S,2E,6R,7aR)-1,6-Dihy-droxy-2-(4-nitro-benzyl-idene)-2,3,5,6,7,7a-hexa-hydro-1H-pyrrolizin-3-one.

Project description:The crystal structure of the title compound, C(14)H(14)N(2)O(5), contains two distinct conformers in the asymmetric unit. The compound has three defined stereocenters, two of them contiguous, and a C=C double bond with an E conformation. The stereocenters exhibit the same chirality in both conformers, with significant differences in the conformation of the five-membered rings of the pyrrolizine unit (both either in a twist or in an envelope form) and in the dihedral angles between the corresponding mean planes and the benzene rings. A prominent feature is a change from almost coplanar rings in one conformer to a new conformation in the second conformer, in which the mean plane of a five-membered ring is almost perpendicular to the benzene ring, with a dihedral angle 87.19 (8)°; the corresponding angle in the first conformer is 14.02 (10)°. In the crystal, molecules are linked by O-H⋯O and C-H⋯O hydrogen bonds. Crystallographic data were essential to confirm the configuration of the double bond, which was unclear from the available two-dimensional NMR data. In addition, reliable Flack and Hooft parameters were obtained, allowing for the correct absolute structure to be determined.

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(1S,2S,6R,7aR)-2-Benzyl-1,6-dihy-droxy-hexa-hydro-pyrrolizin-3-one.

Project description:In the title compound, C(14)H(17)NO(3), the dihedral angles show that the H atoms at two stereocenters are in a trans-diaxial configuration. In the crystal, the molecules are linked by O-H?O hydrogen bonds. The absolute configuration of the molecule has been established on the basis of refinement of the Hooft and Flack parameters.

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(2S*,3S*,3aS*,6S*,7aR*)-3-Hy-droxy-2-[(2R*,3S*)-3-isopropyl-oxiran-2-yl]-3,6-dimethyl-3,3a,5,6,7,7a-hexa-hydro-1-benzofuran-4(2H)-one.

Project description:In the title compound, C(15)H(24)O(4), the six-membered ring shows a distorted chair conformation and the five-membered ring adopts an envelope conformation with the C atom bearing the methyl and OH groups as the flap. In the crystal, O-H?O hydrogen bonds link the mol-ecules into chains running along the a-axis direction.

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