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Communication | Regular issue | Vol 12, No. 11, 1979, pp.1457-1462
Published online, 1st January, 1970
DOI: 10.3987/R-1979-11-1457
Synthesis of Pimprinine and Related Oxazolylindole Alkaloids from N-Acyl Derivatives of Tryptamine and Tryptophan Methyl Ester by DDQ Oxidation

Yuji Oikawa, Tadao Yoshioka, Kunihiko Mohri, and Osamu Yonemitsu*

*Faculty of Pharmaceutical Sciences, Hokkaido University, Kita 12 Nishi 6, Kita-ku, Sapporo, Hokkaido 060-0812, Japan


N-Acyl derivatives of tryptamine and L-tryptophan methyl ester were treated with DDQ under anhydrous conditions directly to give pimprinine and related oxazolylindole alkaloids. Under aqueous conditions, the N-acyl derivatives were readily oxidized to the corresponding β-keto compounds, which were also converted to the oxazolylindoles by the treatment with POCl3.