2014, XIII, 151 p. 257 illus., 24 illus. in color.
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Nominated as an Outstanding Ph.D. thesis by the University College Dublin, Ireland
Development of new methodology combined with target synthesis
Experimental details provided for all transformations-including unpublished results and procedures
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.
Content Level »Research
Keywords »Cyclic Sulfonamides - Generation of All-Carbon Quaternary Centres - Intramolecular Heck Reaction - Multi-Task Catalysis - Natural Product Synthesis - One-Pot Heck Olefination-Hydrogenation Reaction - Overman Rearrangment - Regioselectivity in the Intramolecular Heck Reaction - Synthesis of Sceletium Alkaloids Mesembrane and Mesembrine - Wagner-Meerwein-Type Rearrangement