Literature DB >> 19235819

Total synthesis and absolute configuration of the bisanthraquinone antibiotic BE-43472B.

K C Nicolaou1, Yee Hwee Lim, Jochen Becker.   

Abstract

An-T-biotic: The first total synthesis of the T-shaped bisanthraquinone natural product BE-43472B was accomplished and its absolute configuration assigned. Key transformations in the pivotal cascade sequence include a Diels-Alder reaction, a hemiketal formation, and a nucleophilic aromatic ipso substitution.

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Year:  2009        PMID： 19235819      PMCID： PMC2678724          DOI： 10.1002/anie.200900058

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


  16 in total

1.  Tandem reactions, cascade sequences, and biomimetic strategies in total synthesis.

Authors:  K C Nicolaou; Tamsyn Montagnon; Scott A Snyder
Journal:  Chem Commun (Camb)       Date:  2003-03-07       Impact factor: 6.222

2.  New bisanthraquinone antibiotics and semi-synthetic derivatives with potent activity against clinical Staphylococcus aureus and Enterococcus faecium isolates.

Authors:  Aaron M Socha; Kerry L LaPlante; David C Rowley
Journal:  Bioorg Med Chem       Date:  2006-09-18       Impact factor: 3.641

3.  Total synthesis of (+)-rugulosin and (+)-2,2'-epi-cytoskyrin A through cascade reactions.

Authors:  K C Nicolaou; Yee Hwee Lim; Charles D Papageorgiou; Jared L Piper
Journal:  Angew Chem Int Ed Engl       Date:  2005-12-09       Impact factor: 15.336

Review 4.  Cascade reactions in total synthesis.

Authors:  K C Nicolaou; David J Edmonds; Paul G Bulger
Journal:  Angew Chem Int Ed Engl       Date:  2006-11-06       Impact factor: 15.336

5.  Isoxazole-directed pinacol rearrangement: stereocontrolled approach to angular stereogenic centers.

Authors:  Keisuke Suzuki; Hiroshi Takikawa; Yoshifumi Hachisu; Jeffrey W Bode
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

6.  Total syntheses of 2,2'-epi-cytoskyrin A, rugulosin, and the alleged structure of rugulin.

Authors:  K C Nicolaou; Yee Hwee Lim; Jared L Piper; Charles D Papageorgiou
Journal:  J Am Chem Soc       Date:  2007-03-14       Impact factor: 15.419

7.  The bacteria fight back.

Authors:  Gary Taubes
Journal:  Science       Date:  2008-07-18       Impact factor: 47.728

Review 8.  Catalytic enantioselective Diels--Alder reactions: methods, mechanistic fundamentals, pathways, and applications.

Authors:  E J Corey
Journal:  Angew Chem Int Ed Engl       Date:  2002-05-17       Impact factor: 15.336

9.  Antibiotic bisanthraquinones produced by a streptomycete isolated from a cyanobacterium associated with Ecteinascidia turbinata.

Authors:  Aaron M Socha; Dioscaris Garcia; Roberta Sheffer; David C Rowley
Journal:  J Nat Prod       Date:  2006-07       Impact factor: 4.050

10.  Novel strategies for the synthesis of anthrapyran antibiotics: discovery of a new antitumor agent and total synthesis of (S)-espicufolin.

Authors:  Lutz F Tietze; Kersten M Gericke; Ramakrishna Reddy Singidi; Ingrid Schuberth
Journal:  Org Biomol Chem       Date:  2007-03-14       Impact factor: 3.876
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  10 in total

Review 1.  Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors:  K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal:  Chem Soc Rev       Date:  2012-06-28       Impact factor: 54.564

Review 2.  The art of total synthesis through cascade reactions.

Authors:  K C Nicolaou; Jason S Chen
Journal:  Chem Soc Rev       Date:  2009-04-21       Impact factor: 54.564

3.  Total synthesis: A cascade of new antibiotics.

Authors:  David C Rowley
Journal:  Nat Chem       Date:  2009-05       Impact factor: 24.427

Review 4.  A brief history of antibiotics and select advances in their synthesis.

Authors:  Kyriacos C Nicolaou; Stephan Rigol
Journal:  J Antibiot (Tokyo)       Date:  2017-07-05       Impact factor: 2.649

Review 5.  Antibacterials from the sea.

Authors:  Chambers C Hughes; William Fenical
Journal:  Chemistry       Date:  2010-11-08       Impact factor: 5.236

6.  Recent total syntheses of anthraquinone-based natural products.

Authors:  Jackson A Gartman; Uttam K Tambar
Journal:  Tetrahedron       Date:  2022-01-11       Impact factor: 2.457

7.  Total synthesis and biological evaluation of (+)- and (-)-bisanthraquinone antibiotic BE-43472B and related compounds.

Authors:  K C Nicolaou; Jochen Becker; Yee Hwee Lim; Alexandre Lemire; Thomas Neubauer; Ana Montero
Journal:  J Am Chem Soc       Date:  2009-10-21       Impact factor: 15.419

Review 8.  Novel anti-infective compounds from marine bacteria.

Authors:  Hafizur Rahman; Brian Austin; Wilfrid J Mitchell; Peter C Morris; Derek J Jamieson; David R Adams; Andrew Mearns Spragg; Michael Schweizer
Journal:  Mar Drugs       Date:  2010-03-05       Impact factor: 5.118

Review 9.  Immense essence of excellence: marine microbial bioactive compounds.

Authors:  Ira Bhatnagar; Se-Kwon Kim
Journal:  Mar Drugs       Date:  2010-10-15       Impact factor: 5.118

10.  Two-step synthesis of chiral fused tricyclic scaffolds from phenols via desymmetrization on nickel.

Authors:  Ravindra Kumar; Yoichi Hoshimoto; Eri Tamai; Masato Ohashi; Sensuke Ogoshi
Journal:  Nat Commun       Date:  2017-06-26       Impact factor: 14.919
  10 in total

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