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Synlett 1995; 1995(5): 420-422
DOI: 10.1055/s-1995-4983
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Regioselective Synthesis of 5-endo,6-endo-Dihydroxy-7-Oxabicyclo[2.2.1]heptan-2-one with Differential Protection of the Diol Group

Fabienne Emery, Pierre Vogel*
  • *Section de Chimie de l’Université, BCH-Dorigny, 1015 Lausanne, Switzerland
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Publikationsdatum:
31. Dezember 2000 (online)

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The introduction of two hydroxy groups with differential protection at the endo positions of C(5) and C(6) of the ”naked sugars of the first generation” has been achieved by seleno-Pummerer rearrangement of 5-endo-hydroxy-6-exo-phenylseleno-7-oxabicyclo[2.2.1]heptan-2-one derivatives followed by deselenation with Bu3SnH.

Seleno-Pummerer rearrangement - ”naked sugars” - 5-endo,6-endo-dihydroxy-7-oxabicyclo[2.2.1]heptan-2-one - 5-endo,6-exo-dihydroxy-7-oxabicyclo[2.2.1]heptan-2-one