In the course of our recent study on the gold(I)-catalyzed tandem cyclization of 3-silyloxy 1,6-enynes,1 we discovered unprecedented effects of the olefin geometry and the nature of the silyl groups on the divergence between Pinacol-terminated carbocyclization pathway vs. Claisen-terminated heterocyclization pathway. Progress on the synthesis of alkaloid natural product using this method will be also introduced.
1. Baskar, B.; Bae, H. J.; An, S. E.; Cheong, J. Y.; Rhee, Y. H.; Duschek, A.; Kirsch, S. F. Org. Lett. 2008, 10, 2605.