Synthesis of Pimprinine and Related Oxazolylindole Alkaloids from N-Acyl Derivatives of Tryptamine and Tryptophan Methyl Ester by DDQ Oxidation
Year: 1979
Type: article
Abstract: 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 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
Source: Heterocycles
Authors: Osamu Yonemitsu, Yuji Oikawa, Tadao Yoshioka, Kunihiko Mohri
Institution: Hokkaido University
Language: English
Subfield: Molecular Biology
Domain: Life Sciences
Open Access status: diamond
OpenAlex ID: W4249736902