Tetrahedron p. 1183 - 1190 (1980)
Update date:2022-08-05
Topics:
Kitamura, Tohru
Kawakami, Yosihide
Imagawa, Takeshi
Kawanssi, Mituyosi
Photo-induced rearrangement of 2,3-epoxy-1,4-cyclohexanediones was investigated for a synthesis of γ-alkylidene-γ-butirolactones and γ-alkylidenebutenolides.Irradiation of epoxy diketones 1 and 4 in acetone gave γ-lactones, 2 and 5, and triketones, 3 and 6.On the other hand, in CH2Cl2, EtOAc, or PhH solution epoxy diketones 1 and 4 gave only triketones, 3 and 6.Retro-Diels-Alder reaction of γ-lactones 5aE or 5aZ at 230 deg C (20 mmHg) afforded γ-alkylidenebutenolides 7aE and 7aZ in addition to anthracene.According to the procedure, butelonide 7bZ, a key intermediate for the synthesis of freelingyne, was prepared.The dramatic solvent effect in the photochemical rearrangement was also discussed.
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