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Title: New strategies for chemical synthesis : metal-catalyzed C-H bond functionalisation for complex molecule synthesis
Author: Beck, Elizabeth Mary
Awarding Body: University of Cambridge
Current Institution: University of Cambridge
Date of Award: 2008
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A new method for oxidative palladium (II) catalyzed direct C-H bond alkenylation of pyrroles has been developed, wherein the position of functionalisation can be influenced using a steric and electronic control strategy. Despite the sensitivity of pyrroles towards oxidation and polymerization, the reaction works well for a range of substrates and can proceed under extremely facile and mild conditions using air, oxygen gas or t-BuOOBz as an oxidising system for the palladium. The synthesis of (±)-rhazinicine 1 demonstrates how iterative application of such C-H bond functionalization tactics can positively influence strategic planning in complex molecule assembly. The key motifs are directly installed from a simple pyrrole nucleus using two site-selective catalytic C-H functionalization transformations. The utility of functionalized pyrroles in the synthesis of elaborated pyrrolidines was then investigated through a transannular cyclisation cascade strategy to access (±)-aspidospermindine 3 from the natural product (±)-rhazinilam 2.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available