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Synlett 1990; 1990(8): 485-486
DOI: 10.1055/s-1990-21137
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A Synthesis of Annulated Dihydropyrans via Hetero Diels-Alder Reaction. A Simple Approach to Alboatrin Models

Michael Krause* , H. M. R. Hoffmann
  • *Department of Organic Chemistry, University of Hannover, Schneiderberg 1B, D-3000 Hannover, Federal Republic of Germany
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Publication Date:
08 March 2002 (online)

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Alboatrin model 7 (5-hydroxy-2,3,3a,9a-tetrahydro-4H-furo [2,3-b][1]benzopyran) has been prepared in three steps in 47% overall yield. The three-step synthesis involves a convergent cycloadditon of 1,3-cyclohexanedione, formaldehyde and 2,3-dihydrofuran followed by aromatization of the 3-alkoxy-2-cyclohexenone moiety to an electron rich resorcinol monoether by α-benzeneselenenylation and oxidation with 3-phenyl-2-(p-toluenesulfonyl)oxaziridine (Davis reagent) in the presence of 3,5-dimethoxyaniline.