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Total Synthesis of Putative Chagosensine.
Marc Heinrich1, John J Murphy1, Marina K Ilg1
1Max-Planck-Institut für Kohlenforschung, 45470, Mülheim/Ruhr, Germany.
Angewandte Chemie (International Ed. in English)
|August 29, 2018
Summary
Researchers synthesized the marine macrolide chagosensine, featuring a unique chloro-1,3-diene. Spectral data revealed the isolated compound's structure was misassigned, challenging previous findings.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
- Marine Natural Products
Background:
- Chagosensine is a marine macrolide containing a unique Z,Z-configured chloro-1,3-diene unit.
- The structural elucidation of natural products is crucial for understanding their biological activity and potential applications.
Purpose of the Study:
- To synthesize chagosensine and elucidate its precise chemical structure.
- To investigate novel synthetic methodologies for constructing complex marine natural products.
Main Methods:
- Palladium-catalyzed 1,2-distannation of an alkyne precursor.
- Regioselective Stille cross-coupling and chloro-destannation.
- Cobalt-catalyzed oxidative cyclization for tetrahydrofuran ring formation.
- Yamaguchi macrolactonization for macrocycle closure.
Main Results:
- Successful synthesis of a chagosensine analog incorporating the Z,Z-chloro-1,3-diene moiety.
- Formation of 2,5-trans-disubstituted tetrahydrofuran rings with high selectivity.
- The synthesized compound's spectral data contradicted the initially reported structure of chagosensine.
Conclusions:
- The structure of the marine macrolide chagosensine, as initially reported, has been misassigned.
- This study provides a synthetic route to a unique chloro-diene containing natural product and corrects its structural assignment.
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