Helvetica Chimica Acta p. 2324 - 2331 (1985)
Update date:2022-08-04
Topics:
Matsumoto, Takeshi
Ichihara, Akitami
Yanagiya, Mitsutoshi
Yuzawa, Tamio
Sannai, Akiyoshi
et al.
By a simple process, 3-methoxyjuglone ( = 8-hydroxy-2-methoxy-1,4-naphthoquinone; 9) has been synthesized from 1,2,4-trimethoxybenzene (5) and converted, after prenylation, to α-caryopterone (1; Scheme 1), a pyranojuglone pigment from Caryopteris clandonensis.On the other hand, juglone ( = 5-hydroxy-1,4-naphthoquinone; 12) was regioselectively prenylated at C(2) via its 1-methoxy-cyclohexa-1,3-diene adduct 15 (Scheme 2).The 2-prenyljuglone (4) thus formed led to 1 after oxidation and other reactions.
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