Details
| Original language | English |
|---|---|
| Pages (from-to) | 7335-7338 |
| Number of pages | 4 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 53 |
| Issue number | 28 |
| Publication status | Published - 7 Jul 2014 |
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
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- General Chemistry
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In: Angewandte Chemie - International Edition, Vol. 53, No. 28, 07.07.2014, p. 7335-7338.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - The structure elucidation and total synthesis of β-lipomycin
AU - Hartmann, Olaf
AU - Kalesse, Markus
PY - 2014/7/7
Y1 - 2014/7/7
N2 - 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.
AB - 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.
KW - lipomycins
KW - pentaenes
KW - profile hidden Markov model
KW - structure elucidation
KW - vinylogous Mukaiyama aldol reaction
UR - http://www.scopus.com/inward/record.url?scp=84903791356&partnerID=8YFLogxK
U2 - 10.1002/anie.201402259
DO - 10.1002/anie.201402259
M3 - Article
C2 - 24850084
AN - SCOPUS:84903791356
VL - 53
SP - 7335
EP - 7338
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 28
ER -