Studies toward the synthesis of (-)-anisomycin. The total synthesis of (-)-2-epi-anisomycin

Brann, Paul John (2013) Studies toward the synthesis of (-)-anisomycin. The total synthesis of (-)-2-epi-anisomycin. Doctoral thesis (PhD), University of Sussex.

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Abstract

Exploitation of the asymmetric electron density at the crown of the oxazolidinone [221] allowed for high diastereofacial selectivity when converting the olefin to an epoxide. Regiocontrolled fragmentation of the epoxide enabled us to introduce the three essential stereocentres of the target alkaloid (-)-anisomycin [1] both contiguously and with the correct geometry. Installation of the remaining aromatic appendage allowed us to complete the molecular skeleton of the natural product; however, the synthetic step to facilitate this addition reaction also compromised the chiral integrity of the C2 position. Whilst the desired bioactive alkaloid, (-)-anisomycin [1] was not achieved upon completion of the synthesis, construction of the rare stereoisomer, (-)-2-epi-anisomycin [274] in a 9.4% overall yield demonstrates the routes future potential to deliver (-)-anisomycin [1].

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Item Type: Thesis (Doctoral)
Schools and Departments: School of Life Sciences > Chemistry
Subjects: Q Science > QD Chemistry > QD0241 Organic chemistry
Depositing User: Library Cataloguing
Date Deposited: 06 Dec 2013 12:52
Last Modified: 17 Sep 2015 13:35
URI: http://sro.sussex.ac.uk/id/eprint/47188

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