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Synthesis 2004(9): 1476-1480  
DOI: 10.1055/s-2004-822390
PAPER
© Georg Thieme Verlag Stuttgart · New York

A General Synthesis of N-Reverse-Prenyl Indoles

Fumiaki Yokokawaa, Hideyuki Sugiyamaa, Toyohiko Aoyamaa, Takayuki Shioiri*b
a Graduate School of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori, Mizuho-ku, Nagoya 467-8603, Japan
b Graduate School of Environmental and Human Sciences, Meijo University, Shiogamaguchi, Tempaku, Nagoya 468-8502, Japan
Fax: +81(52)8321555; e-Mail: shioiri@ccmfs.meijo-u.ac.jp;
Further Information

Publication History

Received 14 April 2004
Publication Date:
26 May 2004 (online)

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Abstract

A general method for the construction of N-reverse-prenyl indoles was established using copper catalyzed N-propargyl­ation, the Lindlar hydrogenation of the acetylenic bond, and dehydrogenation with chemical manganese dioxide as key steps. The antifungal indole alkaloids (1 and 2) and N-reverse-prenyl tryptophan (3) were efficiently synthesized by this method.

Key words

N-reverse-prenyl indole - N-propargylation - Lindlar hydrogenation - dehydrogenation

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11

According to the ref. [10] the propargylation reaction proceeded with 0.1 equiv of CuCl. In our case, the reaction proceeded with CuCl but with less efficiency.