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Synthesis 2004(9): 1476-1480
DOI: 10.1055/s-2004-822390
DOI: 10.1055/s-2004-822390
PAPER
© Georg Thieme Verlag Stuttgart · New York
A General Synthesis of N-Reverse-Prenyl Indoles
Further Information
Received
14 April 2004
Publication Date:
26 May 2004 (online)
Publication History
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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References
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.