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(4R,4aS,4bS,5R,10aR*)-4-Hy-droxy-4a,5-dimethyl-2-(propan-2-yl)-1,4,4a,4b,5,6,7,8,10,10a-deca-hydro-phenan-thren-1-one.

ABSTRACT: In the title compound, C(19)H(28)O(2), the A ring adopts a chair conformation. Both the B and C rings adopt envelope conformations with the C atoms common to both rings and adjacent to the carbonyl and hydroxyl groups, respectively, lying 0.604 (3) and 0.634 (3) Å out of the mean planes defined by the remaining five C atoms of rings B and C, respectively (r.m.s. deviations = 0.0100 and 0.0157 Å, respectively). The formation of linear supra-molecular C(7) chains along the a axis mediated by hy-droxy-O-H⋯O(carbon-yl) hydrogen bonds is the most prominent feature of the crystal packing.

SUBMITTER: Caracelli I

PROVIDER: S-EPMC3238985 | biostudies-literature |

REPOSITORIES: biostudies-literature

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(4R,4aS,4bS,7R,10aR)-4-Hy-droxy-4a,7-dimethyl-2-(propan-2-yl)-1,4,4a,4b,5,6,7,8,10,10a-deca-hydro-phenanthren-1-one.

Project description:In the title compound, C(19)H(28)O(2), the A ring adopts a chair conformation, and each of the B and C rings adopts a distorted half-chair conformation with the methine C atom in the CH(2)C(H)C(=O) residue, common to both rings, lying 0.6397 (19) and 0.6328 (18) Å out of the approximate plane defined by the remaining five C atoms (r.m.s. deviations = 0.0791 and 0.0901 Å for rings B and C, respectively). Helical supra-molecular chains along the a axis mediated by hy-droxy-carbonyl O-H⋯O hydrogen bonds feature in the crystal packing.

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Project description:In the title compound, C(19)H(26)O(2), the A ring adopts a chair conformation, whereas the B and C rings both adopt distorted half-chair conformations with the quaternary C atom common to both rings lying 0.577 (3) and 0.648 (3) Å out of the approximate plane defined by the remaining five C atoms (r.m.s. deviations = 0.1386 and 0.1156 Å) for the B and C rings, respectively. Mol-ecules are assembled in the crystal through C-H⋯O inter-actions involving both carbonyl O atoms, which lead to supra-molecular chains aligned along the b axis.

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(4bS,8aS)-1-Isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octa-hydro-phenan-thren-2-yl acetate.

Project description:The hemisynthesis of the title compound, C22H32O2, was carried out through direct acetyl-ation reaction of the naturally occurring diterpene totarol [systematic name: (4bS,8aS)-4b,8,8-trimethyl-1-propan-2-yl-5,6,7,8a,9,10-hexa-hydro-phen-an-thren-2-ol]. The mol-ecule is built up from three fused six membered rings, one saturated and two unsaturated. The central unsaturated ring has a half-chair conformation, whereas the other unsaturated ring displays a chair conformation. The absolute configuration is deduced from the chemical pathway. The value of the Hooft parameter [-0.10 (6)] allowed this absolute configuration to be confirmed.

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Project description:The title compound, C27H34O2, was hemisynthesized through direct benzoyl-ation of the naturally occurring meroterpene totarol. The central fused six-membered ring has a half-chair conformation, whereas the terminal six-membered ring displays a chair conformation. The dihedral angle between the fused benzene ring and the benzoyl benzene ring is 73.05?(14)°. The S,S chirality of the mol-ecule is consistent with the synthetic pathway, and confirmed by the refinement of the Flack parameter.

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Project description:The title compound, C22H28O3, was prepared by a direct acetyl-ation reaction of naturally occurring totarolenone. The mol-ecule contains three fused rings, which exhibit different conformations. The central ring has a half-chair conformation, while the non-aromatic oxo-substituted ring has a screw-boat conformation. In the crystal, mol-ecules are linked by C-H?O hydrogen bonds and C-H?? inter-actions, forming sheets parallel to the bc plane. The carbonyl O atoms and the C atom at the 6-position of the cyclo-hexene ring are each disordered over two sets of sites with major occupancy components of 0.63?(7) and 0.793?(14), respectively.

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