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(1S,2S,4R)-3,3-Dichloro-4,8,12,12-tetra-methyl-tricyclo-[5.5.0.0]dodeca-6,8-diene.

ABSTRACT: The title compound, C(16)H(22)Cl(2), a derivative of ?-himachalene, was semi-synthesized from natural essential oils of Cedrus atlantica. The mol-ecule is built up from two fused six- and seven-membered rings. The six-membered ring has a perfect chair conformation, whereas the seven-membered ring displays a screw boat conformation; the dihedral angle between the rings is 46.48?(9)°.

SUBMITTER: Benharref A

PROVIDER: S-EPMC3007900 | biostudies-literature | 2010 Aug

REPOSITORIES: biostudies-literature

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(1S,2S,4R)-3,3-Dichloro-4,8,12,12-tetra-methyl-tricyclo-[5.5.0.0]dodeca-6,8-diene.

Benharref Ahmed A El Ammari Lahcen L Berraho Moha M Lassaba Esaadia E

Acta crystallographica. Section E, Structure reports online 20100828 Pt 9

The title compound, C(16)H(22)Cl(2), a derivative of β-himachalene, was semi-synthesized from natural essential oils of Cedrus atlantica. The mol-ecule is built up from two fused six- and seven-membered rings. The six-membered ring has a perfect chair conformation, whereas the seven-membered ring displays a screw boat conformation; the dihedral angle between the rings is 46.48 (9)°. ...[more]

PMID: 21588782

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(1S,3R,8S,9R,10S)-2,2-Dichloro-3,7,7,10-tetra-methyl-9,10-ep-oxy-tricyclo-[6.4.0.0]dodeca-ne.

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Project description:The title compound, C(16)H(23)Cl(2)NO, was synthesised from ?-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzocyclo-heptene), which was isolated from the essential oil of the Atlas cedar (Cedrus Atlantica). The mol-ecule contains a seven membered ring, which is fused to a five- and a three-membered ring. The five-membered ring has a twisted conformation, whereas the seven-membered ring displays a chair conformation. The dihedral angle between the five- and seven-membered rings is 45.26?(9)°. The absolute structure was established unambiguously from anomalous dispersion effects. In the crystal, mol-ecules are linked into chains propagating along the b axis by inter-molecular N-H?O hydrogen bonds; an intramolecular N-H?O link also occurs.

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Project description:The title compound, C(15)H(22)O(3), was prepared via amino-acid-promoted Robinson annulation followed by tandem Pd/C-mediated hydrogenation and oxidative cyclization. This product was instrumental in determining the feasibility of a stereocontrolled hydrogenation in which the directing hydroxyl group is adjacent to the 6-7-ring network and its olefinic component. The asymmetric unit consists of a single mol-ecule with normal geometric parameters. The absolute configuration was assigned based on the known enanti-omeric prescursor. Inter-molecular C-H?O inter-actions link each mol-ecule with four neighboring mol-ecules.

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