Journal of Organic Chemistry p. 346 - 349 (1986)
Update date:2022-08-05
Topics:
Yamamoto, Makoto
Iwasa, Seiji
Takatsuka, Kenichi
Yamada, Kazutoshi
A new pyran annelation reaction was investigated. 2,6-Dimethyl-4H-pyran-4-one (2) was converted to 2((p-tolylsulfonyl)methyl)-6-methyl-4H-pyran-4-one (7) which was alkylated at the C-2 methylene position regioselectively, and the p-tolylsulfonyl group can be easily eliminated with an aluminium amalgam reduction.On the other hand the pyran-4-one ring was easily transformed into an 1,5-diketone derivative.By joining and applying these selective alkylations and transformations, tricyclic dienone 22 was effectively synthesized from 2.
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