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Synlett 2000; 2000(11): 1569-1572
DOI: 10.1055/s-2000-7936
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Demonstration of Stereospecificity in the β-Lactone-Initiated Spiroketal Synthesis

Ronald Zemribo* , Keith T. Mead
  • *Department of Chemistry, Mississippi State University, Mississippi State, MS 39762, USA; Fax (6 62) 3 25-16 18; E-mail: kmead@ra.msstate.edu
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Publication Date:
31 December 2000 (online)

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The one-pot spiroketalization of compound 1, terminating with equatorial substitution at the anomeric position, occurs with retention of configuration about the β-lactone stereogenic center and does not involve formation of a spiroketal oxocarbenium ion. A revised mechanism supported by semi-empirical calculations has been proposed for this reaction, consistent with these observations.

spiroketal synthesis - β-lactone - acetal cleavage