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Beilstein J. Org. Chem. 2019, 15, 130–136, doi:10.3762/bjoc.15.13
Graphical Abstract
Figure 1: Diastereomers of LM5CCs, 1a–d.
Figure 2: Diastereomers of LMdiols, 2a–d.
Scheme 1: Dihydroxylation of (a) (R)-limonene and (b) (R)-dihydrolimonene.
Scheme 2: Reduction of LM5CC (1a) and carbonation of LMdiol (2a).
Scheme 3: Overall synthetic routes to LM5CCs and LMdiols. The 93% value (standing for *) from 1d to 2d was ci...
Scheme 4: Plausible conformations of the intermediate in the reaction of LMdiol (2b) with triphosgene.
Figure 3: 1H NMR spectra of LM5CCs 1a–d in CDCl3.
Figure 4: 1H NMR spectra of LMdiols 2a–d in CDCl3.
Figure 5: Plausible conformations of LM5CCs and LMdiols in CDCl3.