Details
| Original language | English |
|---|---|
| Pages (from-to) | 1795-1798 |
| Number of pages | 4 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 53 |
| Issue number | 7 |
| Publication status | Published - 10 Feb 2014 |
Abstract
The impressive biological profile of secondary metabolites isolated from strains of Sorangium cellulosum prompted us to initiate synthetic studies on kulkenon, also isolated from Sorangium cellulosum. The synthesis features a syn-selective vinylogous Kobayashi aldol reaction, recently developed by us, and a ring-closing intramolecular Heck reaction as the pivotal transformations. Comparison of the NMR spectra of the authentic and synthetic material revealed that the proposed configuration had to be revised. A combination of molecular modeling and NOE experiments was used to propose the revised configuration, which was confirmed by a new synthesis. Similar but not identical: The related natural products sulfangolid and kulkenon exhibit different configurations, which only became apparent by synthesizing the proposed structure and comparison with the authentic data. A combination of NOE experiments and computational conformational search identified the correct structure of kulkenon.
Keywords
- Kobayashi aldol reaction, kulkenon, macrolactones, structure elucidation, total synthesis
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- General Chemistry
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In: Angewandte Chemie - International Edition, Vol. 53, No. 7, 10.02.2014, p. 1795-1798.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Structure elucidation and total synthesis of kulkenon
AU - Symkenberg, Gerrit
AU - Kalesse, Markus
PY - 2014/2/10
Y1 - 2014/2/10
N2 - The impressive biological profile of secondary metabolites isolated from strains of Sorangium cellulosum prompted us to initiate synthetic studies on kulkenon, also isolated from Sorangium cellulosum. The synthesis features a syn-selective vinylogous Kobayashi aldol reaction, recently developed by us, and a ring-closing intramolecular Heck reaction as the pivotal transformations. Comparison of the NMR spectra of the authentic and synthetic material revealed that the proposed configuration had to be revised. A combination of molecular modeling and NOE experiments was used to propose the revised configuration, which was confirmed by a new synthesis. Similar but not identical: The related natural products sulfangolid and kulkenon exhibit different configurations, which only became apparent by synthesizing the proposed structure and comparison with the authentic data. A combination of NOE experiments and computational conformational search identified the correct structure of kulkenon.
AB - The impressive biological profile of secondary metabolites isolated from strains of Sorangium cellulosum prompted us to initiate synthetic studies on kulkenon, also isolated from Sorangium cellulosum. The synthesis features a syn-selective vinylogous Kobayashi aldol reaction, recently developed by us, and a ring-closing intramolecular Heck reaction as the pivotal transformations. Comparison of the NMR spectra of the authentic and synthetic material revealed that the proposed configuration had to be revised. A combination of molecular modeling and NOE experiments was used to propose the revised configuration, which was confirmed by a new synthesis. Similar but not identical: The related natural products sulfangolid and kulkenon exhibit different configurations, which only became apparent by synthesizing the proposed structure and comparison with the authentic data. A combination of NOE experiments and computational conformational search identified the correct structure of kulkenon.
KW - Kobayashi aldol reaction
KW - kulkenon
KW - macrolactones
KW - structure elucidation
KW - total synthesis
UR - http://www.scopus.com/inward/record.url?scp=84893632322&partnerID=8YFLogxK
U2 - 10.1002/anie.201309386
DO - 10.1002/anie.201309386
M3 - Article
C2 - 24420412
AN - SCOPUS:84893632322
VL - 53
SP - 1795
EP - 1798
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 7
ER -