Access to a welwitindolinone core using sequential cycloadditions.
A concise approach to the core skeleton of the welwitindolinone alkaloids was developed on the basis of sequential cycloaddition reactions. First, a palladium catalyzed enantioselective [6 + 3] trimethylenemethane cycloaddition onto a tropone nucleus was used to generate the requisite bicyclo[4.3.1]decadiene. Subsequent modifications to the cycloadduct allowed for an intramolecular [4 + 2] cycloaddition to generate the oxindole and complete the core of the natural product family.
Trost
Barry M
BM
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu
McDougall
Patrick J
PJ
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D026121:Indole Alkaloids; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D000078183:Oxindoles; D010165:Palladium / Q000737:chemistry; D014334:Tropolone / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry
D000470:Alkaloids; D026121:Indole Alkaloids; D007211:Indoles; D009570:Nitriles; D000078183:Oxindoles; C507638:welwitindolinone A; C022960:2-oxindole; D010165:Palladium; D014334:Tropolone; C003730:tropone