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Title: Towards the total synthesis of RP-66453
Author: Twiddy, Scott
ISNI:       0000 0004 2734 4591
Awarding Body: University of Southampton
Current Institution: University of Southampton
Date of Award: 2012
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This thesis outlines synthetic work towards the total synthesis of RP-66453, a natural product isolated from a strain of Actinomycetes bacteria which has been shown to bind to the neurotensin antagonist of guinea pigs. The synthesis of several analogues of the biaryl ether macrocycle of RP-66453 have been completed via SNAr ring closure. Our approach employed chiral phase transfer catalyst methodology to synthesise unnatural a-amino acids, which allowed us to develop an efficient and concise route to an advanced intermediate on route to RP-66453. Strategies to form the biaryl macrocycle of RP-66453 are also explored using a model substrate. This led us to modify our original strategy and consider using a phenanthrene intermediate as a surrogate of the A-B macrocycle. This could be formed by a radical or photochemically induced transannular ring contraction.
Supervisor: Harrowven, David Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: QD Chemistry