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

Photochemical rearrangements of highly functionalized longipinene derivatives

DFT and NMR parameterized conformation of valeranone

Cleavage of alkoxycarbonylprotectinggroups from carbamates by t-BuNH2

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

Transesterifications mediated by t-BuNH2

Quirogane, Prenopsane, and Patzcuarane Skeletons Obtained by Photochemically Induced Molecular Rearr...

Synthesis of Indolylindolines Mediated by tert-BuNH2

First Total Synthesis of ()-Flustraminol B

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

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