title: Synthesis of bromoindole alkaloids from Laurencia brongniartii.
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.
authors.affiliation: Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Hidalgo, Apartado 1-622, Pachuca, Hidalgo, 42001 México. osuarez@uaeh.edu.mx
authors.forename: Oscar R
authors.initials: OR
authors.lastname: Suárez-Castillo
authors.forename: Lidia
authors.initials: L
authors.lastname: Beiza-Granados
authors.forename: Myriam
authors.initials: M
authors.lastname: Meléndez-Rodríguez
authors.forename: Alejandro
authors.initials: A
authors.lastname: Alvarez-Hernández
authors.forename: Martha S
authors.initials: MS
authors.lastname: Morales-Ríos
authors.forename: Pedro
authors.initials: P
authors.lastname: Joseph-Nathan
mesh_terms: D018360:Crystallography, X-Ray; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis* / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D044722:Laurencia / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure
chemical_list: D006842:Hydrocarbons, Brominated; D026121:Indole Alkaloids