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Synthesis 1996; 1996(1): 171-177
DOI: 10.1055/s-1996-4158
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Pyranofuranones via Lewis Acid Mediated Hetero-Diels-Alder Reactions of 4-Furan-2(5H)-ones: A Convergent Route to the Manoalide Substructure

E. Lattmann, J. Coombs, H. M. R. Hoffmann*
  • *Department of Organic Chemistry, University of Hannover, Schneiderberg 1 B, D-30167 Hannover, Germany, Fax +49(511)7623011; E-mail hoffmann@mbox.oci.uni-hannover.de
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Publication Date:
31 December 2000 (online)

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A variety of dienes and 4-formylfuran-2(5H)-ones enter into hetero-Diels-Alder reactions. The choice of Lewis acid is decisive and must be tuned to the reactivity of both diene and dienophile. Sensitive cycloadducts are prepared in the presence of Me3Al/AlCl3 and a straightforward route to pyranofuranones is described.

vinylogous glyoxylate - sesterpenoid pharmacophore - PLA2 inhibitor - pericyclic selectivity - bisacetals - bicyclic

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