Chemical and Pharmaceutical Bulletin p. 1588 - 1590 (1996)
Update date:2022-08-11
Topics:
Matsumoto, Takashi
Takeda, Yoshio
Soh, Kimiko
Matsumura, Hiroyuki
Imai, Sachihiko
5,8,11,13-Abietatetraen-3-one (3) and its 12-methoxy derivative (7) were oxidized to the corresponding 3,7-diones, which were rearranged respectively into 2-isopropyl-6-methyl-5-(4-methyl-3-oxopentyl)naphthalene (6) and its 12-methoxy derivative (10) by sodium borohydride reduction and subsequent dehydration with boron trifluoride etherate. Compound 10 was further converted into 3-oxosapriparaquinone (1) via 5-(3-acetoxy-4- methylpentyl)-2-isopropyl-6-methyl-3,4-naphthoquinone (14).
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