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
Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor
Configuration, stereodynamics and crystal structure of 3-substituted-2-oxofuro[2,3-b]indoles
Stereochemical assignment of naturally occurring 2,3-epoxy-2-methylbutanoate esters
One-potsynthesis of conformationallyrestrictedspirooxindoles
Unimolecular rearrangements of ketene-O,O-acetals and fragmentations occurring in the gas phase
Role of lipid peroxidation in biliary obstruction in the rat
Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling