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. 2009 Nov 28;65(Pt 12):o3274.
doi: 10.1107/S1600536809050399.

(3R,4R,5S)-4-Hydr-oxy-3-methyl-5-[(2S,3R)-3-methyl-pent-4-en-2-yl]-4,5-dihydro-furan-2(3H)-one

Annika Gille  1 , Markus Schürmann, Hans Preut, Martin Hiersemann
Affiliations

(3R,4R,5S)-4-Hydr-oxy-3-methyl-5-[(2S,3R)-3-methyl-pent-4-en-2-yl]-4,5-dihydro-furan-2(3H)-one

Annika Gille et al. Acta Crystallogr Sect E Struct Rep Online. .

Abstract

The relative configuration of the title compound, C(11)H(18)O(3), which was synthesized using a catalytic asymmetric Gosteli-Claisen rearrangement, a diastereoselective reduction with K-Selectride and an Evans aldol addition, was corroborated by single-crystal X-ray diffraction analysis. The five-membered ring has an envelope conformation with a dihedral angle of 29.46 (16)° between the coplanar part and the flap (the hydr-oxy-bearing ring C atom). In the crystal, mol-ecules are connected via bifurcated O-H⋯(O,O) hydrogen bonds, generating [010] chains.

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Figures

Fig. 1.
Fig. 1.
: The molecular structure of (I) with displacement ellipsoids shown at the 30% probability level.
See this image and copyright information in PMC

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