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Title: Synthesis of the spirocyclic core of the prunolides using a singlet oxygen-mediated cascade sequence. Author: Sofikiti N, Tofi M, Montagnon T, Vassilikogiannakis G, Stratakis M. Journal: Org Lett; 2005 Jun 09; 7(12):2357-9. PubMed ID: 15932197. Abstract: [reaction: see text] A highly efficient and rapid four-step synthesis of the bis-spiroketal core of the prunolide natural products, starting from furan itself, is described. The key step and culmination of the synthesis, responsible for zipping up the spirocyclic core, is a singlet oxygen-orchestrated cascade sequence in which a double photooxygenation of a 1,2-difuryl alkene precursor precedes dehydration and spirocyclization to furnish the intact prunolide core.[Abstract] [Full Text] [Related] [New Search]