Towards the total synthesis of the azaspiracids

ORGN 856

Jianyan Xu, jxu@chem.umn.edu, Son Nguyen, Yongfeng Li, Feng Zhou, Yue Ding, Shuang Liang, and Craig J. Forsyth, forsyth@chem.umn.edu. Department of Chemistry, University of Minnesota, 207 Pleasant St. SE, Minneapolis, MN 55414

The azapiracids are neurotoxic marine natural products that contaminate cultured shellfish.  Their molecular architectures feature a 40-carbon backbone with a unique array of a structural moieties, including a trioxadispiroketal and an unprecedented spiroaminal fused to a 2,9-dioxabicyclo[3,3,1]nonane ring.  Total synthesis by the Nicolaou group established the complete structures of the azaspiracids.  Progress towards an alternative assembly will be summarized.  This includes highly efficient syntheses of ABCD- and EFGHI-ring containing domains, comprising C1-C20 and C20-C40, respectively.