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Title: Total syntheses of (-)-gephyrotoxin and (±)-morphine
Author: Chu, Shuyu
ISNI:       0000 0004 6499 2731
Awarding Body: University of Oxford
Current Institution: University of Oxford
Date of Award: 2017
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The aim of this DPhil research project is to apply cascade reactions to the total syntheses of gephyrotoxin and morphine. This thesis describes a novel approach towards gephyrotoxin in which the key disconnection is a nucleophilic cascade reaction that constructs the core structure bearing three rings and five stereocentres. This cascade approach enables the total synthesis of gephyrotoxin in nine steps with 14% overall yield. In addition, a new approach towards morphine, involving an ene-yne-ene cascade ring closing metathesis and 1,6-addition to efficiently construct the B/C/D ring systems in a single operation, shortening the synthesis to nine steps with 6.6% overall yield is discussed. The cascade shortcuts enable rapid approaches to these natural products, which results in the most concise total syntheses of gephyrotoxin and morphine described to date.
Supervisor: Smith, Martin D. Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available