A General Synthesis of N-Reverse-Prenyl Indoles

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

References

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  CMD is commercially available from Wako Pure Chemical Industries, Ltd. [Fax: [phone]].

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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.