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Synthetic studies towards garsubellin A: synthesis of model systems and potential mimics by regioselective lithiation of bicyclo[3.3.1]nonane-2,4,9-trione derivatives from catechinic acid

Ahmad, Nadia M., Rodeschini, Vincent, Simpkins, Nigel S., Ward, Simon and Wilson, Claire 2007. Synthetic studies towards garsubellin A: synthesis of model systems and potential mimics by regioselective lithiation of bicyclo[3.3.1]nonane-2,4,9-trione derivatives from catechinic acid. Organic & Biomolecular Chemistry 5 (12) , pp. 1924-1934. 10.1039/b704311b

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Abstract

Bridgehead lithiations have successfully been carried out on substrates derived from catechinic acid, which possess the core bicyclo[3.3.1]nonane-1,3,5-trione structure present in garsubellin A. Using an external quench method, various electrophiles have been incorporated at the C-5 bridgehead position in a one-step process that appears to be sensitive to the substitution pattern on the bicyclic system. Regioselective lithiation at the C-3 sp2 centre was achieved by changing the base used from LDA to LTMP. Following the introduction of a prenyl substituent by bridgehead substitution, annulation of a THF ring, analogous to that in garsubellin A, was possible via an epoxidation–ring opening sequence. Oxidative modification of the catechol substituent of the catechinic acid core was possible to give systems with muconic acid, ortho-quinone or furan 2-carboxylic acid side chains.

Item Type: Article
Date Type: Published Online
Status: Published
Schools: Medicine
Publisher: Royal Society of Chemistry
ISSN: 1477-0520
Date of Acceptance: 25 April 2007
Last Modified: 23 Feb 2018 13:32
URI: http://orca.cf.ac.uk/id/eprint/109403

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