Formal total synthesis of β-pipitzol |
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Authors: | Ignacio H. Sánchez María Isabel Larraza Fernande Basurto Ricardo Yaf?ez Salvador Avila Ricardo Tovar Pedro Joseph-Nathan |
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Affiliation: | nstituto de Química Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, D.F., 04510 México;División de Estudios Superiores, Facultad de Ciencias Químicas e Industriales, Universidad Autónoma del Estado de Morelos, Cuernavaca, MorelosMéxico;Departamento de Química del Centro de Investigación y de Estudios Avanzados, Instituto Politécnico Nacional, P.O. Box 14-740, México, D.F., 07000 México |
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Abstract: | (±)--methylperezone () was obtained by selective oxidative demethylation of (±)-leucoperezone trimethyl ether (). Compound () was prepared by condensation of 2,3,5-trimethoxytoluene () with 6-methyl-5-hepten-2-one, followed by reductive removal of the tertiary alcohol. The aromatic precursor was prepared in four steps from 2,3-dimethoxytoluene () and, alternatively, in three steps from 5-bromoveratraldehyde (). Racemic and were directly compared with the optically active molecules prepared from natural R(-)-perezone (). |
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