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Synthesis of 20-deoxoluteone

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Abstract

20-Deoxoluteone has been synthesized from sclareol. Sclareol was brominated with phosphorus tribromide to form a mixture of primary allyl bromides, from which, by the malonic synthesis, a mixture of bicyclogeranylgeranylacetic acids was obtained which was cyclized with fluorosulfonic acid to form a mixture of two diastereomeric δ-lactones. The predominating lactone was converted by successive reduction with lithium tetrahydroaluminate, oxidation with oxalyl chloride in dimethyl sulfoxide, reaction with methylmagnesium iodide, and oxidation by the chromium trioxide/pyridine complex into 20-deoxyluteone.

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Additional information

Institute of Chemistry, Moldavian SSR Academy of Science, Kishinev. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 346–353, May–June, 1990.

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Vlad, P.F., Ungur, N.D. & Van Hung, N. Synthesis of 20-deoxoluteone. Chem Nat Compd 26, 286–291 (1990). https://doi.org/10.1007/BF00597850

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Keywords

  • Petroleum Ether
  • Lactone
  • Oxalyl Chloride
  • Sclareol
  • Caustic Potash