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Mar. Drugs 2013, 11(7), 2382-2397; doi:10.3390/md11072382
Article

Total Synthesis of Fellutamide B and Deoxy-Fellutamides B, C, and D

1
, 1
, 2
, 2,3
 and 1,*
1 School of Chemistry, The University of Sydney, NSW 2006, Australia 2 Centenary Institute of Cancer Medicine and Cell Biology, Newtown, NSW 2042, Australia 3 Sydney Medical School, The University of Sydney, NSW 2006, Australia
* Author to whom correspondence should be addressed.
Received: 17 April 2013 / Revised: 21 May 2013 / Accepted: 27 May 2013 / Published: 8 July 2013
(This article belongs to the Special Issue Marine Peptides and Their Mimetics)
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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 marine peptides; peptide synthesis; lipopeptide; Mycobacterium tuberculosis; proteasome inhibitors
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

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