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Methyl Homologues of Methyl Jasmonate and Methyl Dihydrojasmonate (Hedione®) from Sorbyl Alcohol

✍ Scribed by Wolfgang Giersch; Iris Farris

Publisher
John Wiley and Sons
Year
2004
Tongue
German
Weight
167 KB
Volume
87
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Treatment of cycloalkanone dimethyl acetals 3–6 with sorbyl alcohol (=(2__E__,4__E__)‐hexa‐2,4‐dien‐1‐ol; 1) in the presence of acids afforded the novel cycloalkenones 8, 9, 11, and 13 via a domino reaction (Claisen rearrangement with intramolecular ene reaction and retro‐ene reaction). Cyclopentenone 8 was readily transformed into 14 and 15, methyl homologues of racemic methyl jasmonate (16) and methyl dihydrojasmonate (=Hedione®; 17), respectively. The organoleptic properties of 14 and 15 are also discussed.

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