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Title: The synthesis of (-)-blepharocalyxin D and other oxygen heterocycles
Author: Cons, Benjamin David
ISNI:       0000 0004 5366 7300
Awarding Body: University of Bristol
Current Institution: University of Bristol
Date of Award: 2014
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This thesis describes the total synthesis of (-)-blepharocalyxin D and related analogues via a novel Prins-type cyclisation that allows the core bicyclic stlUcture to be synthesised in a single step, generating both rings and four new stereocenters. A variety of synthetic routes to y,8-unsaturated alcohols such as 305 were investigated, the key steps in the final route including Wittig olefination, rhodium catalysed 1,4-addition and Chugaev elimination to give 305 which was taken fOlward in the synthesis of 35. In the final chapter, further y,8-unsaturated alcohols were prepared and used in the synthesis of bicyclic lactone 329. Alkene 328 was modified post cyclisation to give a series of novel compounds including protected amine 345. It was found that the reaction of y,8-unsaturated alcohol 106 with aldehydes gave trisubstituted tetrahydropyrans with good stereocontrol. By varying the reaction conditions either an axial or equatorial side-chain was introduced at C-3.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available