Chapter 1 begins with a brief overview of molecular recognition and then presents a review of recently developed methods for lead generation and the synthesis of self-defining host molecules. Chapter 2 describes a strategy for the synthesis of functionally active molecules which combines advantageous features of some of the methods described in Chapter 1. Relevant literature and precedents are then introduced followed by a discussion of theoretical considerations. In Chapter 3, after an introduction to the use of cholate building blocks in supramolecular chemistry, the synthesis of the new steroidal molecules studied is described, together with a discussion of their structural properties. Chapter 4 outlines the development of an effective method for the reversible macrocyclisation of steroidal building blocks by transesterification. The application of this method to the thermodynamically-controlled, and metal ion-templated, cyclisation of the steroid derivatives is then discussed in Chapter 5. An investigation into the metal ion building properties of the steroid derivatives using electrospray mass spectrometry is described in Chapter 6. The chapter begins with initial experiments to explore the circumstances in which the technique can generate meaningful information and then summarises the metal ion binding characteristics of the steroids investigated. Chapter 7 explores transorthoesterification as a milder reversible reaction for the synthesis of macrocycles and then describes initial studies towards a host capable of binding a porphyrin guest. In Chapter 8, the results of the cyclisation experiments and the binding study are compared with each other and put into the wider context of the long term goals of the project. That is followed by some ideas for future directions of this work.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:596861 |
| Date | January 1997 |
| Creators | Brady, P. |
| Publisher | University of Cambridge |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
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