Literature DB >> 20027998

Origins of regioselectivity of Diels-Alder reactions for the synthesis of bisanthraquinone antibiotic BE-43472B.

Amy E Hayden1, Robert S Paton, Jochen Becker, Yee Hwee Lim, K C Nicolaou, K N Houk.   

Abstract

The regioselectivities of several Diels-Alder reactions utilized en route to bisanthraquinone antibiotic BE-43472B are examined using density functional theory calculations. These reactions involve highly substituted dienes and juglone dienophiles, and there is an opposite regiochemical outcome for Diels-Alder reactions with beta-aryl substituted juglones when compared to reactions of unsubstituted juglone. In this article, the effect of an aromatic conjugating group bonded to juglone is explored.

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Year:  2010        PMID： 20027998      PMCID： PMC2813957          DOI： 10.1021/jo902572y

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  9 in total

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3.  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
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Review 5.  Recent advances in the chemistry and biology of naturally occurring antibiotics.

Authors:  K C Nicolaou; Jason S Chen; David J Edmonds; Anthony A Estrada
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6.  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

7.  Regiochemical control in the Diels-Alder reactions of substituted naphthoquinones. Model studies on a regiospecific approach to adriamycinone.

Authors:  T R Kelly; J W Gillard; R N Goerner; J M Lyding
Journal:  J Am Chem Soc       Date:  1977-08-03       Impact factor: 15.419

8.  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

9.  Total synthesis of the proposed structure of the anthrapyran metabolite delta-indomycinone.

Authors:  Lutz F Tietze; Ramakrishna Reddy Singidi; Kersten M Gericke
Journal:  Chemistry       Date:  2007       Impact factor: 5.236
  9 in total
  2 in total

Review 1.  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

2.  Origins of stereoselectivity in the trans Diels-Alder paradigm.

Authors:  Robert S Paton; Joel L Mackey; Woo Han Kim; Jun Hee Lee; Samuel J Danishefsky; K N Houk
Journal:  J Am Chem Soc       Date:  2010-07-14       Impact factor: 15.419
  2 in total

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