Literature DB >> 14703342

Copper-mediated synthesis of N-acyl vinylogous carbamic acids and derivatives: synthesis of the antibiotic CJ-15,801.

Chong Han1, Ruichao Shen, Shun Su, John A Porco.   

Abstract

[reaction: see text] Copper(I)-mediated C-N bond formation has been employed to prepare both N-acyl vinylogous carbamic acids and ureas. The novel N-acyl vinylogous carbamic acid antibiotic, CJ-15,801, was synthesized using this methodology.

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Year:  2004        PMID: 14703342     DOI: 10.1021/ol0360041

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


  14 in total

1.  A stereoselective intramolecular halo-etherification of chiral enamides in the synthesis of halogenated cyclic ethers.

Authors:  Changhong Ko; Richard P Hsung; Ziyad F Al-Rashid; John B Feltenberger; Ting Lu; Jin-Haek Yang; Yonggang Wei; Craig A Zificsak
Journal:  Org Lett       Date:  2007-10-02       Impact factor: 6.005

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.  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

4.  A highly regio- and stereoselective synthesis of α-fluorinated imides via fluorination of chiral enamides.

Authors:  Yan-Shuang Xu; Yu Tang; He-Jing Feng; Ji-Tian Liu; Richard P Hsung
Journal:  Org Lett       Date:  2015-01-12       Impact factor: 6.005

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

Authors:  Maben Ying; William R Roush
Journal:  Tetrahedron       Date:  2011-12-30       Impact factor: 2.457

6.  The antibiotic CJ-15,801 is an antimetabolite that hijacks and then inhibits CoA biosynthesis.

Authors:  Renier van der Westhuyzen; Justin C Hammons; Jordan L Meier; Samira Dahesh; Wessel J A Moolman; Stephen C Pelly; Victor Nizet; Michael D Burkart; Erick Strauss
Journal:  Chem Biol       Date:  2012-05-25

7.  Enamide-benzyne-[2 + 2] cycloaddition: stereoselective tandem [2 + 2]-pericyclic ring-opening-intramolecular N-tethered [4 + 2] cycloadditions.

Authors:  John B Feltenberger; Ryuji Hayashi; Yu Tang; Eric S C Babiash; Richard P Hsung
Journal:  Org Lett       Date:  2009-08-20       Impact factor: 6.005

8.  Stereospecific total synthesis of somocystinamide A.

Authors:  Takashi L Suyama; William H Gerwick
Journal:  Org Lett       Date:  2008-09-13       Impact factor: 6.005

9.  Regio- and stereoselective isomerizations of allenamides: synthesis of 2-amido-dienes and their tandem isomerization-electrocyclic ring-closure.

Authors:  Ryuji Hayashi; Richard P Hsung; John B Feltenberger; Andrew G Lohse
Journal:  Org Lett       Date:  2009-05-21       Impact factor: 6.005

10.  A sequential metal-catalyzed C-N bond formation in the synthesis of 2-amido-indoles.

Authors:  Pei-Yuan Yao; Yu Zhang; Richard P Hsung; Kang Zhao
Journal:  Org Lett       Date:  2008-08-28       Impact factor: 6.005

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