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Literature DB >> 24567066

Cu-mediated enamide formation in the total synthesis of complex peptide natural products.

Takefumi Kuranaga¹, Yusuke Sesoko, Masayuki Inoue.

Abstract

Cu-mediated C(sp(2))-N bond formation has received intense interest recently, and has been applied to the total synthesis of a wide variety of structurally complex natural products. This review covers the synthetic assembly of peptide natural products in which Cu-mediated enamide formation is the key transformation. The total syntheses of cyclopeptide alkaloids, pacidamycin D, and yaku'amide A exemplify the versatility of the Cu-catalyzed cross-coupling reaction in comparison to other synthetic methods.

Entities: Chemical Disease

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Year: 2014 PMID： 24567066 DOI： 10.1039/c3np70103d

Source DB: PubMed Journal: Nat Prod Rep ISSN： 0265-0568 Impact factor: 13.423

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Cited

10 in total

10. Studies on the synthesis of peptides containing dehydrovaline and dehydroisoleucine based on copper-mediated enamide formation.

Authors: Franziska Gille; Andreas Kirschning
Journal: Beilstein J Org Chem Date: 2016-03-22 Impact factor: 2.883

10 in total

Cu-mediated enamide formation in the total synthesis of complex peptide natural products.

1. Isomerization of N-Allyl Amides To Form Geometrically Defined Di-, Tri-, and Tetrasubstituted Enamides.

2. Total synthesis of the reported structure of ceanothine D via a novel macrocyclization strategy.

3. Total Synthesis of the Cyclic Depsipeptide Vioprolide D via its (Z)-Diastereoisomer.

4. Irradiation-induced palladium-catalyzed decarboxylative desaturation enabled by a dual ligand system.

5. Unusual substrate and halide versatility of phenolic halogenase PltM.

6. Metal- and solvent-free synthesis of amides using substitute formamides as an amino source under mild conditions.

7. Towards the total synthesis of chondrochloren A: synthesis of the (Z)-enamide fragment.

8. The Total Synthesis of Chondrochloren A.

9. Ritter-type iodo(iii)amidation of unactivated alkynes for the stereoselective synthesis of multisubstituted enamides.

10. Studies on the synthesis of peptides containing dehydrovaline and dehydroisoleucine based on copper-mediated enamide formation.