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Approaches toward the synthesis of lactonamycin utilising a new benzannulation reaction

Hussain, Jakir

[Thesis]. Manchester, UK: The University of Manchester; 2013.

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Abstract

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.

Layman's Abstract

A novel method for the synthesis of aromatic rings employing CuCl as a catalyst was developed and improved. Attempts were made toward the synthesis of lactonamycin utilising this method. This method can generate naphthalene from benzene, anthracene from naphthalene and many other polyacenes.