The structure elucidation and total synthesis of β-lipomycin.
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.
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).
Olaf
O
Hartmann
Markus
M
Kalesse
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D061065:Polyketides / Q000138:chemical synthesis* / Q000737:chemistry; D011760:Pyrrolidinones / Q000138:chemical synthesis* / Q000737:chemistry
D001688:Biological Products; D061065:Polyketides; D011760:Pyrrolidinones; C000601869:beta-lipomycin
lipomycins; pentaenes; profile hidden Markov model; structure elucidation; vinylogous Mukaiyama aldol reaction