Bulletin of the Chemical Society of Japan p. 324 - 326 (1993)
Update date:2022-08-04
Topics:
Inouye, Yoshinobu
Shirai, Michio
Michino, Tetsuyuki
Kakisawa, Hiroshi
Irradiation of 4,4-dimethyl-3-<(2-cyclopentenyl)methoxy>-2-cyclohexen-1-one, prepared from 4,4-dimethyl-3-phenylthio-2-cyclohexen-1-one and (2-cyclopentenyl)methanol, gave a tetracyclic intramolecular <2+2>-photocycloadduct 7.Treatment of 7 with iodotrimethylsilane followed with tributyltin hydride afforded 3,3,11-trimethylbicyclo<6.3.0>undecane-2,6-dione (12).Methylenation of 12 afforded 6-methylene-3,3,11-trimethylbicyclo<6.3.0>undecan-2-one, the known intermediate to precapnelladiene.
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