Efforts toward the synthesis of (+)-kalkitoxin

CHED 566

Michael T. Corbett, mullinsr@xavier.edu, Adeleke A. Oni, and Richard J. Mullins, mullinsr@xavier.edu. Department of Chemistry, Xavier University, 3800 Victory Parkway, Cincinnati, OH 45207-4221
The lipopeptide (+)-kalkitoxin (1), a metabolite produced by a member of the Lyngbya majuscula family of cyanobacteria, has been shown to exhibit several antiproliferative biological properties. The most noteworthy of these properties is its cytotoxicity to an array of aquatic creatures as well as toxicity to rat neurons and human colon cancer cell lines. On the basis of this interesting bioactivity profile, we have undertaken a complete investigation of the medicinal chemistry of kalkitoxin in order to better understand the manner by which it prevents the growth of tumor cells. Our efforts for the synthesis of kalkitoxin, featuring the application of asymmetric 1,4-conjugate addition reactions, will be presented.