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Synthesis 2013; 45(6): 743-752
DOI: 10.1055/s-0032-1316857
DOI: 10.1055/s-0032-1316857
paper
Total Synthesis of 4-Azaeudistomin Y1 and Analogues by Inverse-ElectronDemand Diels–Alder Reactions of 3-Aminoindoles with 1,3,5-Triazines
Further Information
Publication History
Received: 02 January 2013
Accepted after revision: 24 January 2013
Publication Date:
11 February 2013 (online)
Abstract
A new inverse-electron-demand Diels–Alder (IDA) reaction of 3-aminoindoles as dienophiles was developed for the efficient preparation of 4-aza-β-carbolines in high yields. Because N1-unprotected 3-aminoindoles show poor thermal stability, a one-pot protocol was developed that combines the removal of tert-butoxycarbonyl protecting groups with the IDA reaction. This protocol, using tert-butyl 1H-indol-3-ylcarbamates as reactants, gave the corresponding IDA products in excellent yields. The new IDA methodology was used in a total synthesis of 4-azaeudistomin Y1, which was obtained in 57% overall yield in four steps. Moreover, the chemistry is suitable for the rapid preparation, through either Friedel–Crafts acylation or amide-formation reactions, of analogues that are useful for exploring structure–activity relationships at the C1-position.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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