Producción Científica Profesorado

Synthesis of Bromoindole Alkaloids from Laurencia brongniartii



Meléndez Rodríguez, Myriam

2006

Synthesis of Bromoindole Alkaloids from Laurencia brongniartii. Oscar R. Suárez-Castillo, Lidia Beiza-Granados, Myriam Meléndez-Rodríguez, Alejandro Álvarez-Hernández, Martha S. Morales-Ríos, Pedro Joseph-Nathan. DOI: 10.1021/np060406a


Abstract


A regioselective synthesis of N-carbomethoxy-2,3,5-tribromoindole (6) via a sequential one-pot bromination?aromatization?bromination of N-carbomethoxyindoline (2) is described. The process for the transformation of 2 into 6 permitted the isolation of stable reaction intermediates N-carbomethoxy-5-bromoindoline (3), N-carbomethoxy-5-bromoindole (4), and N-carbomethoxy-3,5-dibromoindole (5). Compound 6 was used to complete the total synthesis of the natural products 1b and 1c. In addition, bromination of N-carbomethoxyindole (11) afforded N-carbomethoxy-2,3,6-tribromoindole (13), from which the natural product 1a was synthesized.



Producto de Investigación




Artículos relacionados

Conformationalstudies of N-carbomethoxy-2-alkoxyindolenines by dynamicNMR, crystallography, and mole...

Synthesis of Indolylindolines Mediated by tert-BuNH2

Mechanisticstudies of the photochemicalrearrangement of 1-oxolongipin-2-ene derivatives

First Total Synthesis of ()-Flustraminol B

Cleavage of alkoxycarbonylprotectinggroups from carbamates by t-BuNH2

DFT and NMR parameterized conformation of valeranone

Transesterifications mediated by t-BuNH2

Synthesis of Bromoindole Alkaloids from Laurencia brongniartii

Regioselective Synthesis of 3-Indolyl(alkoxy)acetates

Photochemical rearrangements of highly functionalized longipinene derivatives