Identification of a novel Michael acceptor group for the reversible addition of oxygen- and sulfur-based nucleophiles. Synthesis and reactivity of the 3-alkylidene-3H-indole 1-oxide function of avrainvillamide.
The 3-alkylidene-3H-indole 1-oxide functional group found in the naturally occurring alkaloid avrainvillamide has been synthesized by a cross coupling-reductive condensation sequence and found to undergo reversible addition of oxygen- and sulfur-based nucleophiles.
D000475:Alkenes / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D000432:Methanol / Q000737:chemistry*; D008958:Models, Molecular; D010087:Oxides / Q000138:chemical synthesis / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013455:Sulfur / Q000737:chemistry
D000475:Alkenes; D007211:Indoles; D010087:Oxides; D013438:Sulfhydryl Compounds; C480558:avrainvillamide; D013455:Sulfur; D010100:Oxygen; D000432:Methanol