Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthetic Studies on Jasmonoids(I): Jasmone, Dihydrojasmone, and Tetrahydrojasmone

  • Lee, Woo-Young (Department of Chemistry, Seoul National University) ;
  • Lee, Yang-Suk (Department of Chemistry, Seoul National University) ;
  • Jang, Se-Young (Department of Chemistry, Seoul National University) ;
  • Lee, Sang-Yong (Department of Chemistry, Seoul National University)
  • Published : 1991.02.20
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Abstract

Facile and efficient syntheses of terpenic perfumeries cis-jasmone, dihydrojasmone, and tetrahydrojasmone have been investigated. Cis-jasmone was synthesized by successive metallation followed by alkylation of acetone N,N-dimethylhydrazone with (Z)-2-penten-1-yl tosylate (or 2-pentyn-1-yl tosylate) and propylene oxide in one flask to give a ketonic alcohol, which was oxidized to the corresponding diketone, followed by base-catalyzed intramolecular aldol condensation to give a regioselective cyclization product. Dihydrojasmone and tetrahydrojasmone could be conveniently obtained from 2-octanone. The dimethylhydrazone of the ketone was lithiated with butyllithium and reacted with propylene oxide to give a ketonic alcohol, which was oxidized to a diketone, followed by base-catalyzed intramolecular cyclization to afford dihydrojasmone. Tetrahydrojasmone was prepared by converting the ketonic alcohol into corresponding iodoketone, followed by base-catalyzed intramolecular cycloalkylation to furnish an odoriferous product.

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References

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