Studies towards the synthesis of ABCD Rings of azaspiracid

ORGN 169

Xiaohua Li, xiaohuachem@hotmail.com and David R. Mootoo, dmootoo@hunter.cuny.edu. Department of Chemistry, The City University of New York, Hunter College, 695 Park Avenue, New York, NY 10021
The marine biotoxin azaspiracid is a structurally intriguing molecule featuring an ABCD ring segment that comprises a trioxodispiroketal fused with a tetrahydrofuran. In preliminary studies towards the synthesis of 1, we have observed that treatment of the cyclopropane—alkene 2 with iodonium dicollidine perchlorate (IDCP) provided the tricyclic product 3 corresponding to the BCD ring system of 1. The incorporation of this result into a synthesis of the ABCD segment of 1 will be presented.