2002
First total syntheses of dihydroflustramine C and flustramine E, alkaloids from the marine bryozoan Flustra foliacea. Morales-Ríos Martha S., Suárez-Castillo Oscar R., Joseph-Nathan P. DOI: http://dx.doi.org/10.1016/S0040-4020(02)00011-X
Abstract
We have developed a simple and practical method for providing the common tricyclic skeleton of physostigmine type alkaloids, and demonstrated its utility for indole alkaloid synthesis. Thus, we achieved the firsttotalsyntheses of ()-dihydroflustramine C and ()-flustramine E, as well as the totalsyntheses of their debromoanalogues from the corresponding 2-hydroxyindolenines in five steps with 31, 27, 39 and 23% overall yields, respectively. The structures of some intermediates were confirmed by single crystal X-ray diffraction analyses.
Trapping enols of esters and lactones with diazomethane
Aromatic Bromination versus Oxidation of Indolylmalonates by Bromine
Stereochemical assignment of naturally occurring 2,3-epoxy-2-methylbutanoate esters
First Total Synthesis of ()-Flustraminol B
Synthesis of Acetamido(indol-3-yl)propanol Derivatives
13C NMR and crystallographic evidence of push-pull effects in furoindolic ?-enamino esters