Abstract
Solanoelcepin A, a triterpenoid hatching stimulant for potato cyst nematode (PCN; Globodera rostochiensis and G. pallida), was first isolated from potato root by Mulder in 1986, and its structure was later determined by Schenk in 1999. As natural hatching stimulus for potato cyst nematode, solaoneclepin A have emerged to be a potential solution for yield loss of potato production over the world. The important biological activity and its complexity of structure have intrigued the interest of synthetic chemists to challenge the total synthesis. This thesis describes the synthesis of an cyclobutane intermediate, which was prepared from ent-Hajos-Parris ketone . The synthesis consists of four key C-C bond formation reactions, including (i)a [2,3]-Wittig rearrangement, (ii) a Michael addition, (iii) a Hg(OTFA)2-mediated oxymercuration/aldol reaction, (iii) the synthesis of cyclobutane intermediate was achieved through a SmI2-mediated radical cyclization, and was carried out in 20 linear synthetic steps with 2.2% yield.