The Total Synthesis of Chondrochloren A
| Autor: | Jan Geldsetzer, Markus Kalesse, Yannick Linne, Christopher Tabet, Elisa Bonandi |
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| Přispěvatelé: | HZI,Helmholtz-Zentrum für Infektionsforschung GmbH, Inhoffenstr. 7,38124 Braunschweig, Germany. |
| Rok vydání: | 2021 |
| Předmět: |
Materials science
010402 general chemistry 01 natural sciences Catalysis Transformation (music) chemistry.chemical_compound Polyketide Computational chemistry Bromide Amide Hoppe anion natural product synthesis 010405 organic chemistry Communication Total synthesis 1 2-metallate rearrangement General Medicine General Chemistry Communications chondrochloren 0104 chemical sciences Coupling (electronics) chemistry Total Synthesis | Hot Paper polyketides |
| Zdroj: | Angewandte Chemie (International ed. in English) Germany Angewandte Chemie (International Ed. in English) |
| ISSN: | 1521-3773 1433-7851 |
| DOI: | 10.1002/anie.202016072 |
| Popis: | The first total synthesis of chondrochloren A is accomplished using a 1,2‐metallate rearrangement addition as an alternative for the Nozaki‐Hiyama‐Kishi reaction. This transformation also avoids the inherent challenges of this polyketide segment and provides a new, unprecedented strategy to assemble polyketidal frameworks. The formation of the Z‐enamide is accomplished using a Z‐selective cross coupling of the corresponding amide to a Z‐vinyl bromide. A powerful alternative to the Nozaki‐Hiyama‐Kishi reaction serves as the key transformation in the total synthesis of chondrochloren A. Using a novel combination of the Hoppe anion in Matteson rearrangements serves to overcome the inherent synthetic challenges of the polyketide portion of chondrochloren A and paves the way to its total synthesis. Remarkably, this transformation can be performed stereoselectively in the absence of sparteine. |
| Databáze: | OpenAIRE |
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