Abstract
The title compound, C11H18O4, consists of an anti,anti,anti-stereo-tetrad with a 1,2-carbonate and an alkene motif. The mol-ecule displays a common zigzag conformation. The five-membered ring has a twisted conformation on the C-C bond. In the crystal, a strong inter-molecular hydrogen bond between the hy-droxy group and the carboxyl-ate moiety from an adjacent mol-ecule forms chains propagating along the b-axis direction. The absolute structure of the mol-ecule in the crystal was determined by resonant scattering [Flack parameter = 0.05 (6)].
Highlights
A strong intermolecular hydrogen bond between the hydroxy group and the carboxylate moiety from an adjacent molecule forms chains propagating along the b-axis direction
The title compound was obtained as part of our studies toward the synthesis of ()-dolabriferol and ()-dolabriferol B
Polypropionate chains are structural motifs consisting of alternating methyl and hydroxy groups within an aliphatic framework (Torres et al, 2004, 2009; Tirado et al, 2005, Rodrıguez et al, 2006)
Summary
The title compound was obtained as part of our studies toward the synthesis of ()-dolabriferol and ()-dolabriferol B (Ciavatta et al, 1996; Jiménez-Romero et al, 2012), using an epoxide-based approach for the stereotetrad construction. Our approach involves a regioselective epoxide cleavage with an alkynyl aluminium reagent (Torres et al, 2005) or Grignard reagent (Rodrıguez et al, 2006), cis or trans reduction of the alkyne (if needed), and the stereoselective epoxidation of the resulting alkenol for the elaboration of each propionate unit.
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