Journal of Organic Chemistry p. 3768 - 3770 (1981)
Update date:2022-08-03
Topics:
Paquette, Leo A.
Annis, Gary D.
Schostarez, Heinrich
Blount, John F.
Through regiocontrolled alkylation of cyclopentanone enolates with methyl 4-bromo-3-methoxycrotonate, base-promoted cyclization, and ketalization, α,β-unsaturated esters having a diquinane molecular framework are produced.Controlled reduction of the carbalkoxy group, application of the Claisen rearrangement, and implementation of an intramolecular Michael addition-oxidation sequence completes a scheme which leads efficiently to tricyclic lactones having structural features common to a number of sesquiterpenoid natural products.
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Doi:10.1016/j.bmcl.2004.07.031
(2004)Doi:10.1071/CH04015
(2004)Doi:10.1007/BF00949725
(1981)Doi:10.1002/ejoc.200400086
(2004)Doi:10.1021/jo0490245
(2004)Doi:10.1007/BF00503329
(1981)
