Total Synthesis of the Polyketide Enterocin

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Total Synthesis of the Polyketide Enterocin
The first chemical total synthesis of the polyketide enterocin was achieved in 22 steps starting from L (+) arabinose with an overall yield of 0.4%. A biomimetic aldol cascade reaction was applied to assemble the rigid tricyclic core of the natural product. After completing the biomimetic total synthesis of enterocin we could determine the previously unknown absolute configuration of the natural product by comparing the synthetic with the naturally occurring material. Die erste Totalsynthese des Polyketids Enterocin wurde in 22 Stufen ausgehend von L-(+)-Arabinose mit einer Ausbeute von 0.4% erreicht. Eine biomimetische Aldoladditions-Sequenz erlaubt es, das starre tricyclische Gerüst des Naturstoffs zu bilden. Nach der erfolgreichen Totalsynthese von Enterocin konnten wir erstmals die Absolutkonfiguration des Naturstoffs durch den Vergleich der synthetischen mit der natürlich vorkommenden Verbindung bestimmen.

More from the series "Organische Chemie"

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ISBN: 9783843953023

Language: English

Publication date: 03.07.2023

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