Journal of the Chemical Society. Perkin transactions I p. 599 - 606 (1981)
Update date:2022-07-31
Topics:
Gill, Melvyn
Rickards, Rodney W.
Terminally functionalised 3-alkyl-4-hydroxycyclopent-2-enones are prepared by conjugate addition-elimination reactions of magnesiocuprate reagents with ethers of 3-chloro-4-hydroxycyclopent-2-enone.The side-chain functionality can be modified either selectivity, or simultaneously with modification of the nucleus.Stereospecific trasposition of the ring-oxygen functions converts these compounds into terminally functionalised 2-alkyl-4-hydroxycyclopent-2-enones which are important intermediates in prostanoid synthesis.Thus the 2-substituted cyclopentenone (2) is prepared in ca. 60percent yield from the 3-chlorocyclopentenone (7), itself available in four steps from phenol.
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