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Synlett 1996; 1996(11): 1065-1066
DOI: 10.1055/s-1996-5688
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Studies in Spiroketal Synthesis 2. A Tandem Cyclization Route to the 1,7-Dioxaspiro[5.5]undecane Ring System

Keith T. Mead* , Ronald Zemribo
  • *Department of Chemistry, Mississippi State University, Mississippi State, MS 39762, USA, Fax 1(601)3251618, e-mail kmead@ra.msstate.edu
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Publication Date:
31 December 2000 (online)

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A novel route to the 1,7-dioxaspiro[5.5]undecane ring system has been demonstrated using a double carbonyl tandem cyclization strategy. The reaction begins with intramolecular β-cleavage of a β-lactone ring by a ketone oxygen, and terminates with nucleophilic addition to a spirooxocarbenium ion.

spiroketals - β-lactones - oxocarbenium ions - silane nucleophiles

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