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Synlett 2001; 2001(12): 1974-1976
DOI: 10.1055/s-2001-18759
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Synthesis of 6-Substituted 4-Hydroxy-2-pyrones from Aldehydes by Addition of an Acetoacetate Equivalent, Dess-Martin Oxidation and Subsequent Cyclization

Thorsten Bach* , Stefan Kirsch
  • *Lehrstuhl für Organische Chemie I, Technische Universität München, Lichtenbergstr. 4, 85747 Garching, Germany; Fax: + 49(89)28913315; E-mail: thorsten.bach@ch.tum.de
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Publication Date:
04 December 2001 (online)

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A three step procedure for the synthesis of 6-substituted 4-hydroxy-2-pyrones 2 from aldehydes 1 is described. An acetoacetate equivalent 3 was added to the corresponding aldehyde (10 examples) in a vinylogous Mukaiyama aldol addition (72-99%). The intermediate alcohols 4 were oxidized to the ketones 5 using the Dess-Martin method (67%-quant.). A final thermal cyclization of compounds 5 yielded the title compounds 2 (61-92%; 40-85% overall).

aldehydes - heterocycles - oxidations - pyrones - ring closure

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