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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.
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.
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