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).
Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2
Aromatic Bromination versus Oxidation of Indolylmalonates by Bromine
The absoluteconfiguration of cuauhtemone and related compounds
Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling
Transesterifications mediated by t-BuNH2
Stereochemical assignment of naturally occurring 2,3-epoxy-2-methylbutanoate esters
Synthesis of Acetamido(indol-3-yl)propanol Derivatives
Absolute configuration determination of 2-(2-oxo-3-indolyl)acetamide derivatives