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

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 met...

Full description

Saved in:
Bibliographic Details
Published inJournal of the American Chemical Society Vol. 130; no. 31; pp. 10293 - 10298
Main Authors Navarro, Ismael, Basset, Jean-François, Hebbe, Séverine, Major, Sarah M, Werner, Thomas, Howsham, Catherine, Bräckow, Jan, Barrett, Anthony G M
Format Journal Article
LanguageEnglish
Published United States 06.08.2008
Subjects
Antifungal Agents - chemical synthesis
Biological Products - chemical synthesis
Biomimetics - methods
Dioxins - chemistry
Esters - chemical synthesis
Ketones - chemistry
Macrolides - chemical synthesis
Resorcinols - chemical synthesis
Zearalenone - chemical synthesis
Online AccessGet full text

Cover

More Information
Summary: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).
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1520-5126
DOI:10.1021/ja803445u