Literature DB >> 26860467

Strategies for construction of the all-carbon macrocyclic skeleton of the ansamycin antibiotic-kendomycin.

Shu Xu1,2, Hirokazu Arimoto3.   

Abstract

Kendomycin, an ansamycin-type natural product first reported in 1996, possesses a series of attractive bioactivities and a unique all-carbon macrocyclic skeleton. To the date, seven total syntheses, two formal total syntheses and a number of synthetic studies on this hot molecule have been reported. In this short review article, we mainly survey and comment on these efforts regarding the difficult macrocyclization strategies.

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Year:  2016        PMID： 26860467     DOI： 10.1038/ja.2016.5

Source DB:  PubMed          Journal:  J Antibiot (Tokyo)        ISSN： 0021-8820            Impact factor:   2.649


  25 in total

1.  Synthetic approach to kendomycin: preparation of the C-glycosidic core.

Authors:  Tetsuya Sengoku; Hirokazu Arimoto; Daisuke Uemura
Journal:  Chem Commun (Camb)       Date:  2004-04-23       Impact factor: 6.222

2.  Strained cyclophane natural products: macrocyclization at its limits.

Authors:  Tanja Gulder; Phil S Baran
Journal:  Nat Prod Rep       Date:  2012-06-25       Impact factor: 13.423

3.  Total synthesis of the antibiotic kendomycin by macrocyclization using photo-Fries rearrangement and ring-closing metathesis.

Authors:  Thomas Magauer; Harry J Martin; Johann Mulzer
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

4.  Interaction of kendomycin and semi-synthetic analogues with the anti-apoptotic protein Bcl-xl.

Authors:  Christian O Janssen; Stephanie Lim; Ee Peng Lo; Kah Fei Wan; Victor C Yu; May Ann Lee; Siew Bee Ng; Martin J Everett; Antony D Buss; David P Lane; Rustum S Boyce
Journal:  Bioorg Med Chem Lett       Date:  2008-09-23       Impact factor: 2.823

5.  Total synthesis of (-)-kendomycin exploiting a Petasis-Ferrier rearrangement/ring-closing olefin metathesis synthetic strategy.

Authors:  Amos B Smith; Eugen F Mesaros; Emmanuel A Meyer
Journal:  J Am Chem Soc       Date:  2005-05-18       Impact factor: 15.419

6.  Total synthesis of kendomycin featuring intramolecular Dötz benzannulation.

Authors:  Kyosuke Tanaka; Masahito Watanabe; Kodai Ishibashi; Hiroshi Matsuyama; Yoko Saikawa; Masaya Nakata
Journal:  Org Lett       Date:  2010-04-16       Impact factor: 6.005

7.  Ring-closing metathesis and photo-fries reaction for the construction of the ansamycin antibiotic kendomycin: development of a protecting group free oxidative endgame.

Authors:  Thomas Magauer; Harry J Martin; Johann Mulzer
Journal:  Chemistry       Date:  2010-01-11       Impact factor: 5.236

8.  Evidence for the mode of action of the highly cytotoxic Streptomyces polyketide kendomycin.

Authors:  Yasser A Elnakady; Manfred Rohde; Florenz Sasse; Christina Backes; Andreas Keller; Hans-Peter Lenhof; Kira J Weissman; Rolf Müller
Journal:  Chembiochem       Date:  2007-07-23       Impact factor: 3.164

9.  A type I/type III polyketide synthase hybrid biosynthetic pathway for the structurally unique ansa compound kendomycin.

Authors:  Silke C Wenzel; Helge B Bode; Irene Kochems; Rolf Müller
Journal:  Chembiochem       Date:  2008-11-03       Impact factor: 3.164

10.  A novel approach toward the synthesis of kendomycin: selective synthesis of a C-aryl glycoside as a single atropisomer.

Authors:  Stefan Pichlmair; Maria M B Marques; Martin P Green; Harry J Martin; Johann Mulzer
Journal:  Org Lett       Date:  2003-11-27       Impact factor: 6.005
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  1 in total

1.  Identification and Heterologous Expression of the Kendomycin B Biosynthetic Gene Cluster from Verrucosispora sp. SCSIO 07399.

Authors:  Jiang Chen; Shanwen Zhang; Yingying Chen; Xinpeng Tian; Yucheng Gu; Jianhua Ju
Journal:  Mar Drugs       Date:  2021-11-26       Impact factor: 5.118
  1 in total

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