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 n class="Chemical">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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