Producción Científica Profesorado

Synthesis of Bromoindole Alkaloids from Laurencia brongniartii Journal of Natural Products

Alvarez Hernandez, Alejandro


Oscar R. Suárez-Castillo, Lidia Beiza-Granados, Myriam Meléndez-Rodríguez, Alejandro Alvarez-Hernandez, Martha S. Morales-Rios and Pedro Joseph-Nathan. Synthesis of Bromoindole Alkaloids from Laurencia brongniartii Journal of Natural Products. 2006, 69, 1596-1600. ISSN 0163-3864. The American Chemical Society. Estados Unidos de América.


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.

Artículos relacionados

Preparation of N-aryl-substituted spiro-?-lactams via Staudinger cycloaddition

Synthesis and Structures of some Lithium and Sodium (Aminoalcoholato)hydrido Aluminates

Et3B, an Efficient Mediator for Xanthate Transfer Based Radical Processes

Structure-Activity Relationships for Inhibition of Cysteine Protease Activity and Development of Pla...

Diastereoselective Synthesis of Spiro-?-lactams via Staudinger Reaction

Highly diastereoselective alkylation, acylation and aldol condensation of cis- and trans-(N-acyloyl)...

Synthesis of New Chiral Derivatives of N,N?-Dimethylpropyleneurea (DMPU) and Examination of Their In...

A flexible access to highly functionalised boronates

Enantioselective synthesis of ?-amino acids. Part 10: Preparation of novel ?,?- and ?,?-disubstitute...

Preparation of Seven- and Eight-Membered Boron Heterocycles from Different Salen Ligands and Arylbor...