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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,*
Received: 17 April 2013; in revised form: 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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MDPI and ACS Style

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.

AMA Style

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.

Chicago/Turabian Style

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.


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