Literature DB >> 21942896

Total synthesis of (±)-streptonigrin: de novo construction of a pentasubstituted pyridine using ring-closing metathesis.

Timothy J Donohoe1, Christopher R Jones, Luiz C A Barbosa.   

Abstract

The synthesis of the potent antitumor agent (±)-streptonigrin has been achieved in 14 linear steps and 11% overall yield from ethyl glyoxalate. The synthesis features a challenging ring-closing metathesis reaction, followed by elimination and aromatization, to furnish a key pentasubstituted pyridine fragment.

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Year:  2011        PMID： 21942896     DOI： 10.1021/ja207835w

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  6 in total

Review 1.  Inverse Electron Demand Diels-Alder Reactions of Heterocyclic Azadienes, 1-Aza-1,3-Butadienes, Cyclopropenone Ketals, and Related Systems. A Retrospective.

Authors:  Jiajun Zhang; Vyom Shukla; Dale L Boger
Journal:  J Org Chem       Date:  2019-05-23       Impact factor: 4.354

2.  Streptonigrin Inhibits SENP1 and Reduces the Protein Level of Hypoxia-Inducible Factor 1α (HIF1α) in Cells.

Authors:  Nigus Ambaye; Chih-Hong Chen; Swati Khanna; Yi-Jia Li; Yuan Chen
Journal:  Biochemistry       Date:  2018-03-01       Impact factor: 3.162

3.  Crystal Structure of StnA for the Biosynthesis of Antitumor Drug Streptonigrin Reveals a Unique Substrate Binding Mode.

Authors:  Tianle Qian; Jing Wo; Yan Zhang; Quanwei Song; Guoqiang Feng; Ray Luo; Shuangjin Lin; Geng Wu; Hai-Feng Chen
Journal:  Sci Rep       Date:  2017-01-11       Impact factor: 4.379

4.  Palladium(II)-Catalyzed Efficient Synthesis of Wedelolactone and Evaluation as Potential Tyrosinase Inhibitor.

Authors:  Huidan Huang; Jianqiu Chen; Jie Ren; Chaofeng Zhang; Fei Ji
Journal:  Molecules       Date:  2019-11-15       Impact factor: 4.411

5.  Total synthesis of the antitumor antibiotic (±)-streptonigrin: first- and second-generation routes for de novo pyridine formation using ring-closing metathesis.

Authors:  Timothy J Donohoe; Christopher R Jones; Anne F Kornahrens; Luiz C A Barbosa; Louise J Walport; Matthew R Tatton; Michael O'Hagan; Akshat H Rathi; David B Baker
Journal:  J Org Chem       Date:  2013-12-12       Impact factor: 4.354

6.  Identification of (2S,3S)-β-Methyltryptophan as the Real Biosynthetic Intermediate of Antitumor Agent Streptonigrin.

Authors:  Dekun Kong; Yi Zou; Zhang Zhang; Fei Xu; Nelson L Brock; Liping Zhang; Zixin Deng; Shuangjun Lin
Journal:  Sci Rep       Date:  2016-02-05       Impact factor: 4.379
  6 in total

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