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

Giersch Wolfgang | Zendy; Farris Iris | Zendy

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

Author(s) -

Giersch Wolfgang,

Farris Iris

Publication year - 2004

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.200490147

Subject(s) - chemistry , methyl jasmonate , intramolecular force , alcohol , cyclopentenone , cinnamates , organoleptic , stereochemistry , methyl salicylate , organic chemistry , medicinal chemistry , botany , biochemistry , food science , gene , biology

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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