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Literature DB >> 10810741

Synthesis of enamides related to the salicylate antitumor macrolides using copper-mediated vinylic substitution

Abstract

[formula: see text] A new approach to the assembly of enamides is described using copper(I) carboxylate-catalyzed substitution of vinyl iodides and amides. Modified reaction conditions have been developed to synthesize the O-methyloxime enamide side chains related to the natural products lobatamides A-F, oximidine I and II, and CJ-12,950.

Entities: Chemical

Year: 2000 PMID： 10810741 DOI： 10.1021/ol005800t

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

14 in total

1. Copper complexes of anionic nitrogen ligands in the amidation and imidation of aryl halides.

Authors: Jesse W Tye; Zhiqiang Weng; Adam M Johns; Christopher D Incarvito; John F Hartwig
Journal: J Am Chem Soc Date: 2008-07-03 Impact factor: 15.419

2. Palladium-catalyzed synthesis of N-vinyl pyrroles and indoles.

Authors: Mohammad Movassaghi; Alison E Ondrus
Journal: J Org Chem Date: 2005-10-14 Impact factor: 4.354

3. Synthesis and biological evaluation of (-)-kunstleramide and its derivatives.

Authors: R Venkateshwarlu; B Chinnababu; U Ramulu; K Purushotham Reddy; M Damoder Reddy; P Sowjanya; P Venkateswara Rao; S Aravind
Journal: Medchemcomm Date: 2016-12-09 Impact factor: 3.597

4. Asymmetric total synthesis and absolute stereochemistry of the neuroactive marine macrolide palmyrolide A.

Authors: Rodolfo Tello-Aburto; Emily M Johnson; Cheyenne K Valdez; William A Maio
Journal: Org Lett Date: 2012-04-04 Impact factor: 6.005

5. Diamine Ligands in Copper-Catalyzed Reactions.

Authors: David S Surry; Stephen L Buchwald
Journal: Chem Sci Date: 2010 Impact factor: 9.825

6. Computational explorations of mechanisms and ligand-directed selectivities of copper-catalyzed Ullmann-type reactions.

Authors: Gavin O Jones; Peng Liu; K N Houk; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2010-05-05 Impact factor: 15.419

Synthesis of enamides related to the salicylate antitumor macrolides using copper-mediated vinylic substitution

1. Copper complexes of anionic nitrogen ligands in the amidation and imidation of aryl halides.

2. Palladium-catalyzed synthesis of N-vinyl pyrroles and indoles.

3. Synthesis and biological evaluation of (-)-kunstleramide and its derivatives.

4. Asymmetric total synthesis and absolute stereochemistry of the neuroactive marine macrolide palmyrolide A.

5. Diamine Ligands in Copper-Catalyzed Reactions.

6. Computational explorations of mechanisms and ligand-directed selectivities of copper-catalyzed Ullmann-type reactions.

7. Studies on the Synthesis of Reidispongiolide A: Stereoselective Synthesis of the C(22)-C(36) Fragment.

8. Pd-catalyzed N-arylation of secondary acyclic amides: catalyst development, scope, and computational study.

9. Total synthesis of TMC-95A and -B via a new reaction leading to Z-enamides. Some preliminary findings as to SAR.

10. Synthetic studies of roquefortine C: synthesis of isoroquefortine C and a heterocycle.