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Title: Approaches toward the synthesis of lactonamycin utilising a new benzannulation reaction
Author: Hussain, Jakir
Awarding Body: University of Manchester
Current Institution: University of Manchester
Date of Award: 2013
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The Bull-Hutchings-Quayle (BHQ) reaction is a novel method for the synthesis of 1-(bromo/chloro)napthalenes from 2-allyphenyl-2’,2’,2’-tri(bromo/chloro)acetates. The reaction is also known as Atom Transfer Radical Cyclisation-Benzannulation (ATRC-Benzannulation). The ATRC-Benzannulation of structurally diverse 2-(cyclohex-1-en-1-ylmethyl)phenyl 2’,2’,2’-trichloroacetates in the presence of 1,3bis-(2,6diisopropylphenyl)imidazolium copper(I) chloride [“Nolan NHC-CuCl”] complexes, using microwave or thermolytic methods, afford a range of 9-chloro-1,2,3,4-tetrahydroanthracenes. Efficient ATRC-Benzannulation has been restricted to microwave conditions so a thermolytic method has been developed as an alternative. Application of BHQ methodology toward the synthesis of the core structure of lactonamycin are reported. Stille, Suzuki and Sonogashira cross-coupling methods were used for the synthesis of diene precursors of a lactonamycin analogue. [4+2] Diels-Alder cycloadditions have been investigated with the diene precursors and various dienophiles. 1-Chloroquinone has been displaced with para-methoxyphenol to generate 1-para-methoxyquinone. CAN mediated oxidation of 1-para-methoxyquinone has yielded 1-hydroxyquinone.
Supervisor: Quayle, Peter Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: ATRC ; Benzannulation ; Aromatic ring synthesis ; Polyacene ; BHQ ; Chloronaphthalene ; Lactonamycin ; Cross-coupling ; Diels-Alder ; Suzuki ; Sonogashira