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(+)-(1S,5R,10S)-11,11-Dimeth­yl-4-oxa­tricyclo­[8.4.0.01,5]tetra­deca­ne-3,12-dione

Authors
Journal
Acta Crystallographica Section E Structure Reports Online
1600-5368
Publisher
International Union of Crystallography
Publication Date
Volume
64
Issue
1
Identifiers
DOI: 10.1107/s1600536807066159
Keywords
  • Organic Papers
Disciplines
  • Mathematics

Abstract

The title compound, C15H22O3, 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.

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