Synthesis of Cyclic α-Diones, a Class of Natural Flavor Compounds

Authors

  • Hannes Wild
  • Ulrich Huber
  • Georg Fráter

DOI:

https://doi.org/10.2533/chimia.1992.399

Abstract

A practical and generally applicable synthesis of the important flavor ingredients corylone (5) and its alkyl homologues 11, 13, 15, and 16 is described, based on alkylation of methyl 4-methoxyacetoacetate (6) with an α-chloro-ketone and subsequent cyclization, hydrolysis, and decarboxylation. The one-pot transformation of methyl 4-chloroacetoacetate to 17 through four consecutive steps is demonstrated. The principle has also been used to prepare the six-membered ring analogues 23 and 24.

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Published

1992-10-30

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