(±)-(1S)-2-(2-Methyl-1,3-dioxolan-2-yl)-1-[(1S)-2-methylenecyclopropyl]-1-ethyl 4-Nitrobenzoate

During the synthesis of paeonilactone B, reaction between lithiated methylenecyclopropane and the appropriate aldehyde [2-(2-methyl-2-dioxolanyl)ethanal] gave the desired alcohol in 65% yield and as a 1:1 mixture of easily separable diastereoisomers. The p-nitrobenzoate ester derived from one diastereoisomer gave the title compound, the crystal structure of which was used to establish the stereochemistry of the precursor alcohol [Boffey et al. (1998). J. Chem. Soc. Chem. Commun. pp. 1875-1876].

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