Ring formation and expansion initiated by gold(I)-alkyne activation

ORGN 451

Steven T. Staben1, Joshua J. Kennedy-Smith2, Jordan Markham1, and F. Dean Toste, fdtoste@berkeley.edu1. (1) Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720-1460, (2) Roche Palo Alto, Palo Alto, CA
Described is the development of a family of gold(I) catalyzed transformations initiated by alkyne activation. 5 exo- and endo- dig enol alkyne cycloisomerizations provide rapid, diastereoselective access to a variety of cyclic systems. Gold(I) catalyzed expansion of alkynylcycloalkanols affords useful alkylidene cycloalkanones. Application of these methods to the synthesis of natural products will be presented.
 

Modern Acetylene Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006