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Angew Chem Int Ed Engl. 2014 Jul 7;53(28):7335-8. doi: 10.1002/anie.201402259. Epub 2014 May 21.

The structure elucidation and total synthesis of β-lipomycin.

Author information

1
Institute for Organic Chemistry and Centre of Biomolecular Drug Research (BMWZ), Leibniz Universität Hannover, Schneiderberg 1B, 30167 Hannover (Germany); Helmholtz Centre for Infection Research (HZI), Inhoffenstrasse 7, 38124 Braunschweig (Germany).

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.

KEYWORDS:

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

PMID:
24850084
DOI:
10.1002/anie.201402259
[Indexed for MEDLINE]

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