Indol-2-one intermediates: mechanistic evidence and synthetic utility. Total syntheses of (+/-)-flustramines A and C.
A variety of 3,3-disubstituted 2-indolinones have been prepared by treatment of 3-bromo-3-alkyl-2-indolinones with dienophiles/nucleophiles in the presence of cesium carbonate. Application of this general strategy has facilitated the total syntheses of the reverse prenylated marine natural products (+/-)-flustramine A and (+/-)-flustramine C. [Structure: see text]
Fuchs
James R
JR
Department of Chemistry, Pennsylvania State University, University Park, PA 16802, USA.
Funk
Raymond L
RL
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D026121:Indole Alkaloids; D007211:Indoles / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure
D000470:Alkaloids; D006575:Heterocyclic Compounds, 3-Ring; D007202:Indicators and Reagents; D026121:Indole Alkaloids; D007211:Indoles; C511648:flustramine C; C456900:indolin-2-one; C041253:flustramine A