Construction of medium ring lactam libraries inspired by octalactin A via ring-closing metathesis

ORGN 304

Keith R. Buszek, buszekk@umkc.edu1, Baohan Xie, xieb@umkc.edu1, Neil Brown1, James K. Mansfield1, Nagaaki Sato2, Yoshi Nakamura1, Youngmee Jeong2, Tiffany L. Coleman1, and Ashley Kearney1. (1) Department of Chemistry, University of Missouri - Kansas City, Spencer Chemical Laboratories, 205 SCB, 5100 Rockhill Road, Kansas City, MO 64110-2481, (2) Department of Chemistry, Kansas State University, 111 Willard Hall, Manhattan, KS 66502
Octalactin A is an architecturally novel and powerful antitumor agent that shows significant activity against a broad spectrum of cancer cell lines. In this presentation the construction of a speculative library of eight-membered lactams inspired by the octalactins is described. The key step for the parallel synthesis of the lactams involves an efficient ring-closing metathesis using the Grubbs second generation catalyst.