Bulletin of the Chemical Society of Japan p. 169 - 173 (1980)
Update date:2022-07-30
Topics:
Hirano, Shigeo
Takagi, Seiji
Hiyama, Tamejiro
Nozaki, Hitosi
Acid-catalyzed reaction of β,β'-disubstituted cross conjugated dienones or the corresponding ethylene acetals gives mainly 2,3-disubstituted 2-cyclopentenones in stead of the simple Nazarov cyclization products, 3,4-disubstituted 2-cyclopentenones.This transformation is explained in terms of electrocyclic ring-closure, addition of hydroxylic solvent(s), tautomerization of the resulting 2-hydroxycyclopentanone intermediates, followed by solvolysis and isomerization.Based on this working hypothesis a new route to jasmonoids is disclosed which involves acid-treatment of the acyloin disilyl ethers derived from substituted glutarates.
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