Concise Access to Heteracenes and Cycloptenanoids through Alkyne Activation: sp to sp2 to sp3 Conversions

Alkynes are considered as one of the simplest and most accessible building blocks in organic chemistry. Manipulation with these modular building blocks enables concise and stereoselective synthesis into sp2- and sp3-rich compounds, which provide new opportunities in material and medical science. Notwithstanding the effort and interest in sp2- and sp3- rich compounds syntheses, progress around these area of research has been hampered by stepwise syntheses of such complicated structures, which effectively increases the cost of mass-production. This thesis presents new synthetic approaches towards both sp2- and sp3-rich molecules via heteroatomic electrophilic activation of alkynes and torquoselective Nazarov cyclization, respectively.