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1 article(s) from Vine, Mark B

Structure and conformational analysis of spiroketals from 6-O-methyl-9(E)-hydroxyiminoerythronolide A

Ana Čikoš,
Irena Ćaleta,
Dinko Žiher,
Mark B. Vine,
Ivaylo J. Elenkov,
Marko Dukši,
Dubravka Gembarovski,
Marina Ilijaš,
Snježana Dragojević,
Ivica Malnar and
Sulejman Alihodžić

Beilstein J. Org. Chem. 2015, 11, 1447–1457, doi:10.3762/bjoc.11.157

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Scheme 1: Synthetic route to spiroketals 2–4. Reaction conditions: a) Na₂S₂O₅/HCOOH/EtOH/water/70 °C, b) DCl/...

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Figure 1: Modelling-derived structure of 2 showing key nOe interactions (calculated distances in Å).

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Figure 2: Time-dependent ¹H NMR spectra of 2, 3 and 4 (13-H multiplets region). The experiments were performe...

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Figure 3: Interconversion kinetics of compounds 2 (blue), 3 (orange) and 4 (grey).

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Figure 4: Modelling-derived structure of 3 showing key nOe interactions (calculated distances in Å).

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Figure 5: Modelling-derived structure of compound 4 showing key nOe interactions (calculated distances in Å).

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Figure 6: Comparison of the spiroketal ring system stereochemistry and conformations in compounds 2–4.

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Figure 7: Overlay of the computed structures of 3 (green) and 4 (blue).

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Scheme 2: Postulated mechanism for the formation of compounds 2–4.

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Published 19 Aug 2015

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