Rhodium(I)-Catalyzed Ring-Closing Reaction of Allene-Alkene-Alkynes: One-Step Construction of Tricyclo[6.4.0.0 2,6 ] and Bicyclo[6.3.0] Skeletons from Linear Carbon Chains.

Treatment of dodecatrienyne derivatives with [RhCl(CO)2 ]2 in refluxing toluene effected the cycloisomerization to produce tricyclo[6.4.0.02,6 ]dodecadienes. The one-carbon shortened undecatrienyne derivatives, however, afforded bicyclo[6.3.0]undecatriene derivatives instead of tricyclic compounds, the latter of which are well known as a basic skeleton of naturally occurring octanoids. On the basis of two experiments with deuterated substrates, a plausible reaction mechanism for the construction of these products was proposed.