In the area of organic chemistry one major challenge we are currently faced with is how to
assemble potentially useful molecules in new ways that generate molecular complexity and in
sequences that are as efficient as possible. Our efforts in this regard specifically for the
preparation of amino containing compounds incorporating an aromatic ring are described in this
doctoral thesis. We discovered an interesting regioselectivity in an intramolecular Heck
reaction which we studied for a series of substrates that are unbiased in terms of the size of
the newly formed ring where very high levels of selectivity in relation to the new
carbon-carbon bond are typically observed. DFT calculations were performed to attempt to shed
light on the reaction sequence. This regioselective Heck reaction combined with the reductive
removal of the temporary amino-protecting group allowed us to synthesize the Sceletium
alkaloids: mesembrane mesembranol and mesembrine.
