Syntheses and odor properties of optically active dimethyl octenone and its analogs

Kawasaki, Masashi; Shimizu, Momo; Kuroyanagi, Saki; Shishido, Yoshiaki; Komiyama, Tsuyoshi; Toyooka, Naoki

doi:10.1016/j.tetasy.2016.02.002

Cited by 6 publications

(1 citation statement)

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“…As an example, they synthesized both enantiomers of a new odorant 1 on the basis of the structure of Cashmeran, a polycyclic musk, and found that the ( R )‐enantiomer ( R )‐ 1 displayed a typical woody–musky Cashmeran odour, and the ( S )‐enantiomer ( S )‐ 1 had no musk odour (Figure ) . Enantiomers of many chemical compounds are perceived differently as odorants . Only ( R )‐ 1 was similar in odour profiles to Cashmeran in spite of the structure of 1 being different from that of Cashmeran.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and olfactory properties of Phantolide analogues in racemic and optically active forms

Kawasaki

Kuroyanagi

Ito

et al. 2018

Flavour & Fragrance J

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The racemates, (+)‐ and (–)‐enantiomers, of eight novel Phantolide analogues, which are non‐natural musk odorants, were synthesized. The key step of the asymmetric synthesis was the lipase‐catalysed enantioselective transesterification of a racemic primary alcohol, and the resultant two enantiomers of the primary alcohol were used as intermediates for further transformations. The odour profiles of all of the synthesized Phantolide analogues were evaluated. Some interesting findings on the odour profiles of the analogues are reported here.

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Section: Introductionmentioning

confidence: 99%