Producción Científica Profesorado

Firsttotalsyntheses of dihydroflustramine C and flustramine E, alkaloids from the marine bryozoan Flustra foliacea



Suárez Castillo, Oscar Rodolfo

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.



Producto de Investigación




Artículos relacionados

One-potsynthesis of conformationallyrestrictedspirooxindoles

Preparation of 3-hydroxyoxindoles with dimethyldioxirane and their use for the synthesis of natural ...

Trapping enols of esters and lactones with diazomethane

Synthesis of ?4:?2-Exocyclic-Diene Iridium(I) Complexes Derived from 1,3-Oxazolidin-2-ones and Their...

Unimolecular rearrangements of ketene-O,O-acetals and fragmentations occurring in the gas phase

First Total Synthesis of ()-Flustraminol B

Regioselective Synthesis of 3-Indolyl(alkoxy)acetates

Stereochemical assignment of naturally occurring 2,3-epoxy-2-methylbutanoate esters

Transesterifications mediated by t-BuNH2

Conformationalstudies of N-carbomethoxy-2-alkoxyindolenines by dynamic NMR, crystallography, and mol...