Synthetic studies of N-reverse prenylated indole. An efficient synthesis of antifungal indole alkaloids and N-reverse prenylated tryptophan

✍ Scribed by Hideyuki Sugiyama; Fumiaki Yokokawa; Toyohiko Aoyama; Takayuki Shioiri

• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 85 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)01492-7

✦ Synopsis

The efficient method for the synthesis of N-1,1-dimethyl-2-propenyl (reverse prenyl) indole was developed by the N-propargylation of the indoline, partial hydrogenation of the terminal alkyne, and oxidation to the indole using chemical manganese dioxide (CMD). This method was used for the synthesis of the antifungal indole alkaloids 2, 3, and N-reverse prenylated tryptophan.