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. 2016 Sep 21;14(35):8367-75.
doi: 10.1039/c6ob01233g. Epub 2016 Aug 17.

Total synthesis of fellutamides, lipopeptide proteasome inhibitors. More sustainable peptide bond formation

Michael C Pirrung  1 , Fa Zhang, Sudhakar Ambadi, Y Gangadhara Rao
Affiliations

Total synthesis of fellutamides, lipopeptide proteasome inhibitors. More sustainable peptide bond formation

Michael C Pirrung et al. Org Biomol Chem. .

Erratum in

Abstract

Solution-phase syntheses of three bioactive natural products of mixed polypeptide-polyketide biogenesis, fellutamides A, B, and C, have been achieved. Three peptide bonds are generated without the use of coupling reagents in each synthesis of the fellutamides, which act against proteasomes.

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Figures

Scheme 1
Scheme 1
Peptide synthesis via NCAs and ester ligations
Scheme 2
Scheme 2
Synthesis of a fellutamide advanced intermediate
Scheme 3
Scheme 3
Synthesis of β-hydroxydodecanoic acid lactone
Scheme 4
Scheme 4
Synthesis of fellutamides C and B
Scheme 5
Scheme 5
Preparation of fellutamide A intermediate 13
Scheme 6
Scheme 6
Completion of the synthesis of fellutamide A
See this image and copyright information in PMC

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