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Preparation of the Zaragozic Acid Core through Rearrangement of an Oxonium Ylide

  • Brogan, John B.
  • Zercher, Charles K.
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Publication date
March 1998
Icon DOI
10.1016/S0040-4039(98)00127-0
Publisher
University of New Hampshire Scholars\u27 Repository

Abstract

The diastereoselective formation of a 2,8-dioxabicyclo[3.2.1]octane skeleton was accomplished through the generation and rearrangement of a bicyclic oxonium ylide. The skeleton which was formed is common to the zaragozic acid family and possesses appropriate functionality for further manipulation. The study also revealed the first example of an exocyclic 2,3-shift from a acetal-derived oxonium ylide

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