Journal of the Chemical Society. Perkin transactions I p. 159 - 162 (1990)
Update date:2022-08-03
Topics:
Clawson, Paul
Lunn, Patricia M.
Whiting, Donald A.
The styrene oxides (14) and (15), bearing electron-withdrawing functions, readily undergo thermal and photochemical (triplet sensitised) dipolar cycloadditions with simple electron-deficient olefins, regioselectively in the case of methyl acrylate.However, cycloadditions with 5-arylbutenolides as dipolarophiles, required for lignan synthesis, could not be effected in significant yield.A new short route to 5-arylbut-2-enolides was devised.The dihydro- and tetrahydro-furan adducts (18d), (19d), and (20d) all fragment in base to the dienol nitrile (25).
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Doi:10.1016/S0040-4020(01)82377-2
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