This thesis explores the use of cyclic alkenylsiloxanes in Hiyama cross-coupling reactions for the stereospecific construction of the Z-pentaenyl system of incednam, the aglycon of incednine. The early chapters continue the investigation of the previously developed C6-C13 lynchpin cyclic diethyl alkenylsiloxane, accessed by controlled semi-hydrogenation of alkynylsiloxane. Later chapters discuss the development of a novel strategy to access the more reactive cyclic dimethyl alkenylsiloxanes and their application towards the synthesis of incednam.