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.
Artículos relacionados
Synthesis of Bromoindole Alkaloids from Laurencia brongniartii
Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling
The absoluteconfiguration of cuauhtemone and related compounds
Stereochemical assignment of naturally occurring 2,3-epoxy-2-methylbutanoate esters
Transesterifications mediated by t-BuNH2
13C NMR and crystallographic evidence of push-pull effects in furoindolic ?-enamino esters
Synthesis of Indolylindolines Mediated by tert-BuNH2
Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor