title: A [3+2] dipolar cycloaddition route to 3-hydroxy-3-alkyl oxindoles: an approach to pyrrolidinoindoline alkaloids.
abstract: A [3 + 2] cycloaddition approach to the 3-hydroxy-3-alkyl oxindole scaffold is described. Isoxazolines obtained by cycloaddition of nitrile oxide 3 with 3-methylene oxindoles were elaborated to 3-hydroxy-3-cyanomethyl oxindoles employing a one-pot protocol en route to the pyrrolidinoindoline moiety which is found in many natural products. The total syntheses of alkaloids (±)-alline and (±)-CPC-1 were achieved using this methodology.
authors.affiliation: Sanford-Burnham Medical Research Institute at Lake Nona, Conrad Prebys Center for Chemical Genomics, 6400 Sanger Road, Orlando, Florida 32827, USA.
authors.forename: Anand
authors.initials: A
authors.lastname: Singh
authors.forename: Gregory P
authors.initials: GP
authors.lastname: Roth
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D000478:Alkylation; D000605:Amino Alcohols / Q000737:chemistry; D003500:Cyclization; D006900:Hydroxylation; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D000078183:Oxindoles; D011758:Pyrroles / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D000605:Amino Alcohols; D007211:Indoles; D000078183:Oxindoles; D011758:Pyrroles; C022960:2-oxindole