Total Synthesis of Patulone: A Natural Xanthonoid Possessing a Geminally Diisoprenylated Structure
Synlett（2023）
Abstract
The first total synthesis of patulone, a plant metabolite possessing a unique 1,1-diisoprenyl-1H-xanthene-2,9-dione structure, is described. Starting from a 1-fluroxanthone derivative with suitable substitution pattern, the pivotal gem-diisoprenylation was efficiently accomplished by implementing twice the sequence of addition of isoprenyl Grignard reagent to the carbonyl at C9 and anion-accelerated oxyCope rearrangement.
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Key words
total synthesis,xanthone,geminal substitution,isoprenylation,oxy-Cope rearrangement,regioselectivity
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