Totallsynthese des Carotinoidbutenolids Peridinin
eBook - PDF

Totallsynthese des Carotinoidbutenolids Peridinin

Vom Diethyltartrat Ăźber ?-Bromacrylate zu ?-Alkylidenbutenoliden

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  1. 528 pages
  2. English
  3. PDF
  4. Available on iOS & Android
eBook - PDF

Totallsynthese des Carotinoidbutenolids Peridinin

Vom Diethyltartrat Ăźber ?-Bromacrylate zu ?-Alkylidenbutenoliden

,

About this book

Ziel dieser Arbeit war die stereoselektive Synthese des Carotinoidbutenolids Peridinin (10), das eine Schlßsselrolle in der Photosynthese von Plankton spielt. Die Strategie fßr die Synthese des ?-Alkylidenbutenolidteils von Peridinin (10) war, Weinsäurediethylester (226) als C4-Baustein einzusetzen. Die syn-Diol-Gruppe von 226 stellte dabei den Vorläufer fßr eine stereoselektive ?-Eliminierung von Wasser zum Aufbau der Z-konfigurierten C?=C1'-Doppelbindung dar. Als zweiter Baustein fßr den Butenolidring sollte ein Reagenz 155 zur stereoselektiven Synthese von (E)-?-Bromacrylaten (E)-58 zum Einsatz kommen, das während der Reaktionssequenz an ein Derivat von Diethyltartrat (226) angeknßpft werden sollte. Das nach der Olefinierung (1. in Schema 144) entstandene (E)-?-Bromacrylat (E)-58 erlaubt dabei zum einen, die Lactonisierung des Esters zum Butenolid und zum anderen eine Palladium-katalysierte Kupplung des Bromatoms mit einem Epoxid-Baustein.

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Information

Publisher
Cuvillier Verlag
Year
2006
Print ISBN
9783865377814
eBook ISBN
9783736917811
Edition
1

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