Producción Científica Profesorado

Preparation of O-Methyl Substituted 2-Oxofuro- and 2-Oxopyrrolidinoindolines by Reductive Lactonization of Oxindol-3-ylacetic Acids



Suárez Castillo, Oscar Rodolfo

2012

Morales-Rios, MS; Rivera-Becerril, E; Lopez-Camacho, PY ; Perez-Rojas, NA ; Suarez-Castillo, OR, Preparation of O-Methyl Substituted 2-Oxofuro- and 2-Oxopyrrolidinoindolines by Reductive Lactonization of Oxindol-3-ylacetic Acids, NATURAL PRODUCT COMMUNICATIONS. Año: 2012 Volume: 7 Issue: 11 Pages: 1445-1451.ISSN: 1934-578X


Abstract


A practical procedure for the preparation of O-methyl substituted 3a,8-dialkyl-2-oxofuroindolines is described. Reductive lactonization of the corresponding oxindol-3-ylacetic acids provides a route for the formation of this class of compounds. Further transformation of 2-oxofuroindolines into 2-oxopyrrolidinoindolines, and then to pyrrolidinoindolines demonstrates their versatility as key intermediates in natural products synthesis. The results of single-crystal X-ray crystallographic analyses are given for five of the studied compounds.






Artículos relacionados

13C NMR and crystallographic evidence of push-pull effects in furoindolic ?-enamino esters

Cascade [1,3]-Sigmatropic Rearrangements of Ketene O,O-Acetals: Kinetic and DFT Level Mechanistic St...

Synthesis of Bromoindole Alkaloids from Laurencia brongniartii

Reactivity of TpMe2Ir(C2H4)(DMAD) with carboxylic acids. A DFT study on geometrical isomers and stru...

The absoluteconfiguration of cuauhtemone and related compounds

Regioselective Synthesis of 3-Indolyl(alkoxy)acetates

Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling

Synthesis of Acetamido(indol-3-yl)propanol Derivatives

Firsttotalsyntheses of dihydroflustramine C and flustramine E, alkaloids from the marine bryozoan Fl...

Trapping enols of esters and lactones with diazomethane