Synthesis of Pimprinine and Related Oxazolylindole Alkaloids from N-Acyl Derivatives of Tryptamine and Tryptophan Methyl Ester by DDQ Oxidation
1979; Elsevier BV; Volume: 12; Issue: 11 Linguagem: Inglês
10.3987/r-1979-11-1457
ISSN1881-0942
AutoresOsamu Yonemitsu, Yuji Oikawa, Tadao Yoshioka, Kunihiko Mohri,
Tópico(s)Cyclopropane Reaction Mechanisms
ResumoN-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 3-keto compounds, which were also converted to the oxazolylindoles by the treatment with POC13.Pimprinine , an alkaloid having antieplepticl and monoamine oxidase inhibitory activitles,2 was first isolated from Streptomyces pimprina3 and synthesized
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