Tetrahedron p. 2355 - 2359 (1985)
Update date:2022-08-03
Topics:
Sanchez, Ignacio H.
Larraza, Maria Isabel
Basurto, Fernando
Yanez, Ricardo
Avila, Salvador
et al.
(+/-)-O-methylperezone (1b) was obtained by selective oxidative demethylation of (+/-)-leucoperezone trimethyl ether (4a).Compound (4a) was prepared by condensation of 2,3,5-trimethoxytoluene (5e) with 6-methyl-5-heptene-2-one, followed by reductive removal of the tertiary alcohol.The aromatic precursor 5e was prepared in four steps from 2,3-dimethoxytoluene (5a) and, alternatively, in three steps from 5-bromoveratraldehyde (6a).Racemic 1b and 4a were directly compared with the optically active molecules prepared from natural R(-)-perezone (1a).
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