Abstract
The photo-reaction of 9-oxabicyclo[3.3.1]nonan-3-one (2) was investigated. Upon irradiation in methanol, the ketone (2) predominantly gave the methanol adduct, 3-hydroxymethyl-9-oxabicyclo[3.3.1]nonan-3-ol (3), accompanied with photo-reduced products, exo- and endo-9-oxabicyclo[3.3.1]nonan-3-ol (4 and 5). Irradiation in water resulted in Norrish type I cleavage to give directly (cis-6-methyletrahydropyran-2-yl)acetic acid (1), a constituent of civet, in moderate yield.
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