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1 article(s) from Pillainayagam, Terence A

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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Graphical Abstract

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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