2007
First total synthesis of ()-flustraminol B.Oscar R. Suárez-Castillo, Maricruz Sánchez-Zavala, Myriam Meléndez-Rodríguez, Eliazar Aquino-Torres, Martha S. Morales-Ríos, Pedro Joseph-Nathan. DOI: 10.3987/COM-07-11048
Abstract
A first route for the synthesis of a 6-brominated marine alkaloid, flustraminol B (1), is reported using 2,6-dibromoindole (3b) as a key starting material. Bromine atoms were introduced regioselectively to 2b using NBS. The crucial selective reductive cyclization of the corresponding 6-brominated-2,3-dioxindole (7b) was successfully controlled using Red-Al in toluene, leading to 6-brominated pyrroloindole (8), which by selective N-methylation gave flustraminol B (1).
Trapping enols of esters and lactones with diazomethane
Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling
Aromatic Bromination versus Oxidation of Indolylmalonates by Bromine
Absolute configuration determination of 2-(2-oxo-3-indolyl)acetamide derivatives
Unimolecular rearrangements of ketene-O,O-acetals and fragmentations occurring in the gas phase
Transesterifications mediated by t-BuNH2
Total Syntheses of Five Indole Alkaloids from the Marine Bryozoan Flustra foliacea
Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor