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Tandem Enyne Metathesis-Diels−Alder Reaction for Construction of Natural Product Frameworks

2004; American Chemical Society; Volume: 69; Issue: 6 Linguagem: Inglês

10.1021/jo0356311

1520-6904

Marta Rosillo, Gema Domı́nguez, Luis Casarrubios, Ulises Amador, Javier Pérez‐Castells,

Chemical Synthesis and Analysis

Enynes connected through aromatic rings are used as substrates for metathesis reactions. The reactivity of three ruthenium carbene complexes is compared. The resulting 1,3-dienes are suitable precursors of polycyclic structures via a Diels−Alder process. Some domino RCM-Diels−Alder reactions are performed, suggesting a possible beneficial effect of the ruthenium catalyst in the cycloaddition process. Other examples require Lewis acid cocatalyst. When applied to aromatic ynamines or enamines, a new synthesis of vinylindoles is achieved. Monitorization of several metathesis reactions with NMR shows the different behavior for ruthenium catalysts. New carbenic species are detected in some reactions with an important dependence on the solvent used.