A General Synthesis of N-Reverse-Prenyl Indoles

Fumiaki Yokokawa; Hideyuki Sugiyama; Toyohiko Aoyama; Takayuki Shioiri

doi:10.1055/s-2004-822390

PAPER

A General Synthesis of N-Reverse-Prenyl Indoles

Fumiaki Yokokawa^a, Hideyuki Sugiyama^a, Toyohiko Aoyama^a, 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;

Abstract

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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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References

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