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Total Synthesis of Fellutamide B and Deoxy-Fellutamides B, C, and D
School of Chemistry, The University of Sydney, NSW 2006, Australia
Centenary Institute of Cancer Medicine and Cell Biology, Newtown, NSW 2042, Australia
Sydney Medical School, The University of Sydney, NSW 2006, Australia
* Author to whom correspondence should be addressed.
Received: 17 April 2013; in revised form: 21 May 2013 / Accepted: 27 May 2013 / Published: 8 July 2013
Abstract: The total syntheses of the marine-derived lipopeptide natural product fellutamide B and deoxy-fellutamides B, C, and D are reported. These compounds were accessed through a novel solid-phase synthetic strategy using Weinreb amide-derived resin. As part of the synthesis, a new enantioselective route to (3R)-hydroxy lauric acid was developed utilizing a Brown allylation reaction followed by an oxidative cleavage-oxidation sequence as the key steps. The activity of these natural products, and natural product analogues was also assessed against Mycobacterium tuberculosis in vitro.
Keywords: marine peptides; peptide synthesis; lipopeptide; Mycobacterium tuberculosis; proteasome inhibitors
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Giltrap, A.M.; Cergol, K.M.; Pang, A.; Britton, W.J.; Payne, R.J. Total Synthesis of Fellutamide B and Deoxy-Fellutamides B, C, and D. Mar. Drugs 2013, 11, 2382-2397.
Giltrap AM, Cergol KM, Pang A, Britton WJ, Payne RJ. Total Synthesis of Fellutamide B and Deoxy-Fellutamides B, C, and D. Marine Drugs. 2013; 11(7):2382-2397.
Giltrap, Andrew M.; Cergol, Katie M.; Pang, Angel; Britton, Warwick J.; Payne, Richard J. 2013. "Total Synthesis of Fellutamide B and Deoxy-Fellutamides B, C, and D." Mar. Drugs 11, no. 7: 2382-2397.