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1. Biomimetic synthesis of resorcylate natural products utilizing late stage aromatization: concise total syntheses of the marine antifungal agents 15G256iota and 15G256beta.

Author

Navarro I, Basset JF, Hebbe S, Major SM, Werner T, Howsham C, Bräckow J, and Barrett AG

Subjects
Biological Products chemical synthesis, Dioxins chemistry, Esters chemical synthesis, Ketones chemistry, Resorcinols chemical synthesis, Zearalenone chemical synthesis, Antifungal Agents chemical synthesis, Biomimetics methods, Macrolides chemical synthesis
Abstract

Diketo-1,3-dioxin-2-ones underwent retro-Diels-Alder reaction on heating in toluene at 110 degrees C to generate alpha,gamma,-triketo-ketenes. These were trapped with alcohols to provide 2,4,6-triketocarboxylates, which were smoothly aromatized by sequential reaction with potassium carbonate and methanolic hydrogen chloride to give resorcylate esters. The reaction was applied in the total synthesis of the marine antifungal agents 15G256beta (1), 15G256iota (2), and 15G256pi (3) and the mycotoxin S-(-)-zearalenone (4).

Published
2008
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