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Title: Towards the total synthesis of anthracimycin
Author: Lodovici, Giacomo
ISNI:       0000 0004 7964 6516
Awarding Body: University of York
Current Institution: University of York
Date of Award: 2019
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In 2013 W. Fenical et al. reported the isolation of a natural product from a marine microorganism of streptomyces species, which possessed significant activity against Gram-positive pathogens Bacillus anthracis, methicillin-resistant and vancomycin resistant Staphylococcus aureus (MRSA).15 The compound responsible for the antibiotic activity was found to be the 14-membered macrolide named anthracimycin. The research detailed in this thesis describes the efforts towards the total synthesis of this natural product and specifically the formation of the core of anthracimycin in 12-steps. Direct palladium catalysed oxidation formed the enone used as a dienophile in a stereo- and regio-selective Diels‒Alder/epimerisation sequence, which afforded the trans-decalin. A facial and stereoselective Hosomi‒Sakurai 1,4-addition reaction, followed by a selective borylation/dihydroxylation sequence on the exocyclic alkene, allowed the formation of the core of anthracimycin.
Supervisor: Clarke, Paul Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available