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Title: The development of one-pot multi-reaction processes for the synthesis of natural products and biologically active compounds
Author: Calder, Ewen D. D.
ISNI:       0000 0004 5354 0721
Awarding Body: University of Glasgow
Current Institution: University of Glasgow
Date of Award: 2015
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This thesis is divided into four chapters in which one-pot processes have been developed and utilised for the synthesis of biologically active compounds. The work in the first chapter outlines the 13-step total synthesis of D -ribo- and L - arabino-phytosphingosine from D -ribose. This process employed a microwave promoted Overman rearrangement of an allylic trichloroacetimidate to install the amine functionality. In the second and third chapters, the development of a one-pot, two-step Overman/ring closing metathesis process is detailed. The synthesis of three different classes of starting material is also shown. This one-pot process was used as the key step in the synthesis of four oxybenzo[c]phenanthridine natural products and the partial synthesis of an ACAT inhibitor. The potential for further functionalisation of the products by oxidation and reduction was also explored. In the final chapter, a one-pot allylboration/Heck process for the synthesis of indan-1-ols is described. Optimisation and an investigation of the scope of the process are also presented. The process was then altered to allow the use of a chiral phosphoric acid catalyst for the asymmetric synthesis of these compounds.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: QD Chemistry