| סיכום: | <p>This thesis details the optimisation and development to the synthesis of the ABC fragment of pectenotoxin-4, a 26-membered macrolide marine natural product bearing 19 stereogenic centres, three tetrahydrofuran rings, one spiroketal and one bicyclic ketal.</p> <p><b>Introduction</b></p> <p>This section briefly discusses the isolation, structure elucidation, and biological activity of penctenotoxins, along with a review of previous synthetic efforts on the pectenotoxin family, especially the ABC fragment. It also summarises our group’s work in pursuing the total synthesis of this compound.</p> <p><b>Results and Discussion</b></p> <p>This section details synthetic efforts to improve the overall yield of the ABC fragment. In particular, it contains the optimisation of a low yield Carreira alkynylation reaction and a revised protecting group strategy to allow orthogonal deprotection on the ABC fragment for further elaborations. The revised route for the ABC fragment of pectenotoxin-4 contains 21 longest linear steps (27 steps in total) from D-mannitol with an overall yield of 2.1% (on average 83% per step).</p>
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