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Beilstein J. Org. Chem. 2015, 11, 1447–1457, doi:10.3762/bjoc.11.157
Graphical Abstract
Scheme 1: Synthetic route to spiroketals 2–4. Reaction conditions: a) Na2S2O5/HCOOH/EtOH/water/70 °C, b) DCl/...
Figure 1: Modelling-derived structure of 2 showing key nOe interactions (calculated distances in Å).
Figure 2: Time-dependent 1H NMR spectra of 2, 3 and 4 (13-H multiplets region). The experiments were performe...
Figure 3: Interconversion kinetics of compounds 2 (blue), 3 (orange) and 4 (grey).
Figure 4: Modelling-derived structure of 3 showing key nOe interactions (calculated distances in Å).
Figure 5: Modelling-derived structure of compound 4 showing key nOe interactions (calculated distances in Å).
Figure 6: Comparison of the spiroketal ring system stereochemistry and conformations in compounds 2–4.
Figure 7: Overlay of the computed structures of 3 (green) and 4 (blue).
Scheme 2: Postulated mechanism for the formation of compounds 2–4.