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2 article(s) from Light, Mark E

Aldol elaboration of 4,5,6,7-tetrahydroisoxazolo[4,3-c]pyridin-4-ones, masked precursors to acylpyridones

Raymond C. F. Jones,
Abdul K. Choudhury,
James N. Iley,
Mark E. Light,
Georgia Loizou and
Terence A. Pillainayagam

Beilstein J. Org. Chem. 2012, 8, 308–312, doi:10.3762/bjoc.8.33

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Figure 1: The 3-acyl-4-hydroxypyridin-2-one motif, example natural products and the isoxazolopyridone scaffol...

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Scheme 1: Aldol reactions of tetrahydroisoxazolopyridone 6. Reagents: (i) LDA–TMEDA, RCHO, THF, −20 °C; (ii) ...

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Figure 2: X-ray crystal structure of 3-(2-phenylethenyl)-4,5,6,7-tetrahydroisoxazolo[4,3-c]pyridin-4-one (8a) ...

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Figure 3: Ilicicolin H as an example of a 3-decalinoyl-4-hydroxypyridin-2-one metabolite.

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Scheme 2: Retrosynthetic analysis of a model 3-decalinyl-4,5,6,7-tetrahydroisoxazolopyridone 10.

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Scheme 3: Synthesis of triene 11. Reagents: (i), LDA, propenal, THF, −78 °C; (ii), LiAlH₄, THF, 20 °C (75%); ...

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Published 27 Feb 2012

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NMR studies of anion-induced conformational changes in diindolylureas and diindolylthioureas

Damjan Makuc,
Jennifer R. Hiscock,
Mark E. Light,
Philip A. Gale and
Janez Plavec

Beilstein J. Org. Chem. 2011, 7, 1205–1214, doi:10.3762/bjoc.7.140

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Figure 1: Anion receptors 1–4 together with their atomic numbering scheme.

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Figure 2: ¹H NMR spectra of 1 in the absence of anions (a) and upon addition of one equivalent of the followi...

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Figure 3: Three representative conformational families of rotamers of 1. Notations refer to the orientations ...

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Figure 4: NOE enhancements of 1 in the absence of anions (a) and upon addition of one equivalent of acetate a...

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Figure 5: Surface plot of the relative potential energy of 1 as a function of the two constitutive [C6–C7–N7α...

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Figure 6: Freely optimized structure at the B3LYP/6-311+G(d,p) level of theory and side view showing deviatio...

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Figure 7: ¹H NMR chemical shift changes, Δδ = δ (in the presence of anions) – δ (in the absence of anions), i...

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Figure 8: Freely optimized structures at the B3LYP/6-311+G(d,p) level of theory and side view showing deviati...

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Figure 9: Conformational preferences and proposed binding mode for the 3·AcO⁻ 1:1 complex.

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Published 02 Sep 2011

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