Received 30 April 2010
In the title compound, C18H20O4, both the tetrahydropyranone ring and the cyclohexene ring adopt envelope conformations. The crystal packing is stabilized by weak intermolecular C-HO hydrogen bonding.
The title compound is a derivative of 1-oxo-hexahydro-1H-isochromene, which has been reported as a key intermediate towards the total syntheses of natural products such as eleutherobin and tetronothiodin, see: Kim et al. (2000); Jung et al. (2000); Page et al. (2003). For microwave-assisted intramolecular Diels-Alder cycloaddition, see: Wu et al. (2006, 2007); Wang et al. (2009).
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2757 ).
This work is supported by the Natural Science Foundation of China (grant No. 20572092). Professor Wei-Min Dai is thanked for his valuable suggestions on this work. Mr Jianming Gu of the X-ray crystallography facility of Zhejiang University is acknowledged for his assistance with the crystal structure analysis.
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