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Report | Regular issue | Vol 22, No. 2, 1984, pp.371-374
Published online, 1st January, 1970
DOI: 10.3987/R-1984-02-0371
A Development of Pictet-Spengler Reaction in Aprotic Media Using Chloroformates; a Short Synthesis of Borrerine

Etsuji Yamanaka, Naoki Shibata, and Shin-ichiro Sakai*

*Faculty of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan

Abstract

Pictet-Spengler reaction between tryptamine (1) and aldehydes (2a,b) was achieved through the intermediates (5a,b,c) in the presence of chloroformates to give the β-carbolines (6a,b,c), which were converted to the amines (7a,b) and the natural alkaloid, borrerine (8).