Literature DB >> 22644891

Stereoselective total syntheses of herbicidin C and aureonuclemycin through late-stage glycosylation.

Dominik Hager1, Peter Mayer, Christian Paulitz, Jörg Tiebes, Dirk Trauner.   

Abstract

Better late than never! Two herbicidins, members of an important family of nucleoside antibiotics, have been synthesized for the first time. The route integrates a stereoselective C-glycosylation with several reagent-controlled stereoselective transformations and a surprisingly facile and highly diastereoselective late-stage N-glycosylation.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID: 22644891     DOI: 10.1002/anie.201201826

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  5 in total

1.  Elucidation of the Herbicidin Tailoring Pathway Offers Insights into Its Structural Diversity.

Authors:  Hai-Xue Pan; Zhang Chen; Tianfang Zeng; Wen-Bing Jin; Yujie Geng; Geng-Min Lin; Juan Zhao; Wei-Tao Li; Zijun Xiong; Sheng-Xiong Huang; Xin Zhai; Hung-Wen Liu; Gong-Li Tang
Journal:  Org Lett       Date:  2019-02-14       Impact factor: 6.005

2.  Crystallization-Enabled Henry Reactions: Stereoconvergent Construction of Fully Substituted [N]-Asymmetric Centers.

Authors:  Pedro De Jesús Cruz; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2022-08-18       Impact factor: 16.383

3.  Identification and Interrogation of the Herbicidin Biosynthetic Gene Cluster: First Insight into the Biosynthesis of a Rare Undecose Nucleoside Antibiotic.

Authors:  Geng-Min Lin; Anthony J Romo; Priscilla H Liem; Zhang Chen; Hung-Wen Liu
Journal:  J Am Chem Soc       Date:  2017-11-08       Impact factor: 15.419

4.  Synthesis and antibacterial activity of doxycycline neoglycosides.

Authors:  Jianjun Zhang; Larissa V Ponomareva; Karen Marchillo; Maoquan Zhou; David R Andes; Jon S Thorson
Journal:  J Nat Prod       Date:  2013-08-29       Impact factor: 4.050

5.  Herbicidin congeners, undecose nucleosides from an organic extract of Streptomyces sp. L-9-10.

Authors:  Xingyun Chai; Ui Joung Youn; Dianqing Sun; Jingqiu Dai; Philip Williams; Tamara P Kondratyuk; Robert P Borris; Julian Davies; Ivan G Villanueva; John M Pezzuto; Leng Chee Chang
Journal:  J Nat Prod       Date:  2014-02-17       Impact factor: 4.050

  5 in total

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