Aryllead(IV) reagents in synthesis: formation of the C11 quaternary center of N-methylwelwitindolinone C isothiocyanate.
The reaction of lead(IV) 4-indolyl triacetate with substituted methyl 2-oxo-1-cyclohexanecarboxylates has been investigated as a route to the natural product N-methylwelsitindolinone C isothiocyanate. Reaction of lead(IV) reagent 18 with beta-ketoester 20 affords the desired coupled material in excellent yield and diastereoselectivity. Reaction: see text.
Deng
H
H
Department of Chemistry and Biochemistry, University of California, Santa Cruz, CA 95064, USA.
Konopelski
J P
JP
D020168:ATP Binding Cassette Transporter, Subfamily B, Member 1 / Q000037:antagonists & inhibitors; D000470:Alkaloids / Q000138:chemical synthesis*; D000935:Antifungal Agents / Q000138:chemical synthesis; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D000458:Cyanobacteria / Q000737:chemistry; D018432:Drug Resistance, Multiple; D026121:Indole Alkaloids; D007854:Lead / Q000737:chemistry
D020168:ATP Binding Cassette Transporter, Subfamily B, Member 1; D000470:Alkaloids; D000935:Antifungal Agents; D000970:Antineoplastic Agents; D026121:Indole Alkaloids; C092268:N-methylwelwitindolinone C isothiocyanate; D007854:Lead