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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 (CC BY 3.0).

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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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