Synthesis and odor description of optically active cyclopropanated analogues of geraniol, nerol, nor-leaf alcohol, and matsutake alcohol

Hiroki Asao, Hiroyuki Sakauchi, Shigefumi Kuwahara, Hiromasa Kiyota

    Research output: Contribution to journalArticlepeer-review

    9 Citations (Scopus)

    Abstract

    Both enantiomers of cyclopropanated analogues of geraniol, nerol, nor-leaf alcohol, and matsutake alcohol were synthesized and their odor properties evaluated. Odor characters in enantiomeric pairs were similar in the geraniol series. The (+)-(2R,3S)-nerol derivative showed various odor aspects. From the results of nor-leaf alcohol derivatives, an interaction between the (2-re,3-re)-face of nor-leaf alcohol and the human olfactory receptor was suggested. The odor of (3R)-matsutake alcohol derivative was superior to the enantiomer.

    Original languageEnglish
    Pages (from-to)537-541
    Number of pages5
    JournalTetrahedron Asymmetry
    Volume18
    Issue number4
    DOIs
    Publication statusPublished - 2007 Mar 12

    ASJC Scopus subject areas

    • Catalysis
    • Physical and Theoretical Chemistry
    • Organic Chemistry
    • Inorganic Chemistry

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