Producción Científica Profesorado

First Total Synthesis of ()-Flustraminol B



Suárez Castillo, Oscar Rodolfo

2007

First total synthesis of ()-flustraminol B.Oscar R. Suárez-Castillo, Maricruz Sánchez-Zavala, Myriam Meléndez-Rodríguez, Eliazar Aquino-Torres, Martha S. Morales-Ríos, Pedro Joseph-Nathan. DOI: 10.3987/COM-07-11048


Abstract


A first route for the synthesis of a 6-brominated marine alkaloid, flustraminol B (1), is reported using 2,6-dibromoindole (3b) as a key starting material. Bromine atoms were introduced regioselectively to 2b using NBS. The crucial selective reductive cyclization of the corresponding 6-brominated-2,3-dioxindole (7b) was successfully controlled using Red-Al in toluene, leading to 6-brominated pyrroloindole (8), which by selective N-methylation gave flustraminol B (1).



Producto de Investigación




Artículos relacionados

Stereochemical assignment of naturally occurring 2,3-epoxy-2-methylbutanoate esters

Preparation of 3-hydroxyoxindoles with dimethyldioxirane and their use for the synthesis of natural ...

Trapping enols of esters and lactones with diazomethane

Transesterifications mediated by t-BuNH2

Role of lipid peroxidation in biliary obstruction in the rat

Unimolecular rearrangements of ketene-O,O-acetals and fragmentations occurring in the gas phase

The absoluteconfiguration of cuauhtemone and related compounds

Conformationalstudies of N-carbomethoxy-2-alkoxyindolenines by dynamic NMR, crystallography, and mol...

Absolute configuration determination of 2-(2-oxo-3-indolyl)acetamide derivatives

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