With the aid of novel synthetic methodologies and new analytical techniques, studies on natural products opened a new era of pharmaceutical science. In many cases, these candidates are derivatives of the active compound of the natural product synthesis.

Octalactin A, a novel eight-membered lactone-containing natural product with potent cytotoxic properties, was isolated from marine bacterium, Pacifigorgia sp., which lives in association with a type of octacoral. Its isolation and structure determination were reported by Fenical and Clardy in 1991.¹ In 1994, the first total synthesis of octalactin A was achieved by Buszek.² The Buszek laboratory published another approach to octalactin A via the ring closing metathesis (RCM) method in 2002³ and continued the research on the novel medium-ring libraries. The research presented in this thesis is focused on the synthesis of a speculative eight-membered lactam library inspired by octalactin A.