Gold-catalyzed synthesis of the azaspiracid ABCD ring system

ORGN 914

Yongfeng Li, yli@chem.umn.edu, Feng Zhou, and Craig J Forsyth, forsyth@chemistry.ohio-state.edu. Department of Chemistry, University of Minnesota, 207 Pleasant St. SE, Minneapolis, MN 55455

The azaspiracids comprise a family of marine toxins responsible for human poisoning events.  Biological studies showed that the azaspiracids could cause severe damage to the liver, pancreas, thymus and spleen in mice.  The structure of azaspiracid-1 was first proposed by Yasomuto et al. in 1998 and later revised by Nicolaou et al. in 2004 upon completion of a total synthesis.  In our synthetic approach towards these natural products, a novel gold (I) catalyzed etherfication was employed to construct the A-D ring bisspiroketal system.  This will be presented in the context of our total synthesis efforts.