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(+)-(1S,5R,10S)-11,11-Dimeth­yl-4-oxa­tricyclo­[8.4.0.0(1,5)]tetra­deca­ne-3,12-dione

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 grou...

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Detalles Bibliográficos
Autores principales: Gallucci, Judith C., Inomata, Kohei, Dura, Robert D., Paquette, Leo A.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2007
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2915339/
https://www.ncbi.nlm.nih.gov/pubmed/21200853
http://dx.doi.org/10.1107/S1600536807066159
Descripción
Sumario: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 mol­ecule with normal geometric parameters. The absolute configuration was assigned based on the known enanti­omeric prescursor. Inter­molecular C—H⋯O inter­actions link each mol­ecule with four neighboring mol­ecules.