Roridin E

Roridin E is a mycotoxin of the trichothecene group. In nature it is mainly found in fungi of the Fusarium and Myrothecium species. The Fusarium and Myrothecium species belong to the most prevalent mycotoxin producing species in south-east Asia and Australia, therefore making them a considerable risk for the food crop production industry. The fungi are abundant in various agricultural products (cereal crops) and their further processed products such as bread. The Fusarium and Myrothecium species invade and grow on crops, and may produce roridin E under moist and cool conditions. In rats, the symptoms observed after exposure to roridin E and linoleic acid are increased blood glucose levels and a decrease in glutathione. This may attribute to the toxic effect of roridin E due to its ability to delay the absorption and elimination of the mycotoxin.

Roridin E is a mycotoxin of the trichothecene group. In nature it is mainly found in fungi of the Fusarium and Myrothecium species. The Fusarium and Myrothecium species belong to the most prevalent mycotoxin producing species in south-east Asia and Australia, therefore making them a considerable risk for the food crop production industry. The fungi are abundant in various agricultural products (cereal crops) and their further processed products such as bread. The Fusarium and Myrothecium species invade and grow on crops, and may produce roridin E under moist and cool conditions. In rats, the symptoms observed after exposure to roridin E and linoleic acid are increased blood glucose levels and a decrease in glutathione. This may attribute to the toxic effect of roridin E due to its ability to delay the absorption and elimination of the mycotoxin. Roridin E is produced via a coupling between a verrucarol molecule and a macrocyclization of a carbon chain, as shown in the reaction scheme below. This entails a series of steps whereby the secondary alcohol is converted into the desired carboxylic acid via a Jones oxidation yielding compound 2. In an additional step, the alcohol of verrucarol on carbon 15 is esterified selectively by adding compound 2, DCC, and 4-pyrrolidinopyridine (4-pp). And the alcohol on carbon 4 was converted to the desired phosphono ester, yielding compound 3. Then the cyclopentylidene was removed and a diol was produced. This diol was then cleaved, deformylated, and treated with excess (formylmethylene)triphenylphosphorane, resulting in the formation of an aldehyde and yielding compound 4. Macrocyclization was accomplished by using finely ground potassium carbonate and 18-crown-6, yielding compound 5. In the final step, compound 5 was treated with potassium tert-butoxide in isopropyl alcohol. These conditions resulted in a conjugation of the C3'=C4' olefin to yield the final compound roridin E.

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