Literature DB >> 24850084

The structure elucidation and total synthesis of β-lipomycin.

Olaf Hartmann1, Markus Kalesse.   

Abstract

Here we describe the synthesis of β-lipomycin, a secondary metabolite isolated from the fermentation broth of Corallococcus coralloides. The synthesis relies on the structural assignment made by a statistical method, the so-called profile hidden Markov model. Using this protocol, not only the configuration of the secondary alcohol, but also of the adjacent methyl branch could be deduced. The synthesis therefore not only provides access to this natural product but also confirms the validity of this approach for configurational assignment at methyl branches of modular polyketides.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  lipomycins; pentaenes; profile hidden Markov model; structure elucidation; vinylogous Mukaiyama aldol reaction

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Year:  2014        PMID: 24850084     DOI: 10.1002/anie.201402259

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


  4 in total

Review 1.  Insights into polyketide biosynthesis gained from repurposing antibiotic-producing polyketide synthases to produce fuels and chemicals.

Authors:  Satoshi Yuzawa; Jay D Keasling; Leonard Katz
Journal:  J Antibiot (Tokyo)       Date:  2016-06-01       Impact factor: 2.649

2.  Stereochemical Assignment of the Protein-Protein Interaction Inhibitor JBIR-22 by Total Synthesis.

Authors:  Alan R Healy; Miho Izumikawa; Alexandra M Z Slawin; Kazuo Shin-Ya; Nicholas J Westwood
Journal:  Angew Chem Weinheim Bergstr Ger       Date:  2015-02-04

3.  Towards the total synthesis of chondrochloren A: synthesis of the (Z)-enamide fragment.

Authors:  Jan Geldsetzer; Markus Kalesse
Journal:  Beilstein J Org Chem       Date:  2020-04-14       Impact factor: 2.883

4.  The Total Synthesis of Chondrochloren A.

Authors:  Yannick Linne; Elisa Bonandi; Christopher Tabet; Jan Geldsetzer; Markus Kalesse
Journal:  Angew Chem Int Ed Engl       Date:  2021-02-25       Impact factor: 15.336

  4 in total

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