Producción Científica Profesorado

Formal synthesis of (?)-flustramine B and its absolute configuration assignment by vibrational circular dichroism exciton chirality



Suárez Castillo, Oscar Rodolfo

2015

Formal synthesis of (?)-flustramine B and its absolute configuration assignment by vibrational circular dichroism exciton chirality, Reyna E. Cordero-Rivera, Myriam Meléndez-Rodríguez, Oscar R. Suárez-Castillo, Claudia I. Bautista-Hernández, Nayely Trejo-Carbajal, Julián Cruz-Borbolla, Luis E. Castelán-Duarte, Martha S. Morales-Ríos, Pedro Joseph-Nathanb, Tetrahedron Asymmetry, doi:10.1016/j.tetasy.2015.05.009


Abstract


A formal synthesis of the natural product (?)-flustramine B (3) is described, together with an easy and reliable approach for the absolute configuration assignment of a series of (3R,14S)- and (3S,14S)-oxindolylacetylphenyloxazolidinones 4, 6, 13a?c, and amides (+)- and (?)-14 by evaluation of the vibrational circular dichroism bisignated couplet resulting from the interaction of the C2 and C9 carbonyl groups. The absolute configuration assignment was validated by 1H NMR spectra and X-ray diffraction, and therefore (?)-flustramine B 3 was established as (3aS,8aR)-3.



Producto de Investigación




Artículos relacionados

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

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

One-potsynthesis of conformationallyrestrictedspirooxindoles

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

Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor

Trapping enols of esters and lactones with diazomethane

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

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

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

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