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).
Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor
13C NMR and crystallographic evidence of push-pull effects in furoindolic ?-enamino esters
Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling
First Total Synthesis of ()-Flustraminol B
The absoluteconfiguration of cuauhtemone and related compounds
Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2
Stereochemical assignment of naturally occurring 2,3-epoxy-2-methylbutanoate esters
Absolute configuration determination of 2-(2-oxo-3-indolyl)acetamide derivatives