Syntheses and odor descriptions of cyclopropanated compounds part 5. Analogs of methyl jasmonate to fix the relative configuration of the two side chains

Hiromasa Kiyota, Shin Ya Takigawa, Shigefumi Kuwahara

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Abstract

Analogs of methyl jasmonate (=methyl (1R*,2R*)-3-oxo-2-[(Z)- pent-2-enyl]cyclopentaneacetate; MJA) bearing a cyclopropane ring, double bond, or a F-substituent were synthesized, and their odor characteristics were examined. Most of the analogs with the same stereochemical properties as methyl epijasmonate showed odor properties superior to MJA. Interestingly, the enol acetate of MJA had a diffusive orchid-like note.

Original languageEnglish
Pages (from-to)1854-1859
Number of pages6
JournalHelvetica Chimica Acta
Volume87
Issue number7
DOIs
Publication statusPublished - 2004
Externally publishedYes

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ASJC Scopus subject areas

  • Chemistry(all)

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