Two New Syntheses of the Pyranojuglone Pigment α??Caryopterone
T Matsumoto, A Ichihara, M Yanagiya…
Index: Matsumoto, Takeshi; Ichihara, Akitami; Yanagiya, Mitsutoshi; Yuzawa, Tamio; Sannai, Akiyoshi; et al. Helvetica Chimica Acta, 1985 , vol. 68, p. 2324 - 2331
Full Text: HTML
Citation Number: 17
Abstract
Abstract 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 ...
Related Articles:
Regiospecific addition of monooxygenated dienes to halo quinones
[Boisvert, Louise; Brassard, Paul Journal of Organic Chemistry, 1988 , vol. 53, # 17 p. 4052 - 4059]