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Synthesis 1995; 1995(12): 1517-1520
DOI: 10.1055/s-1995-4132
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Synthesis of (1S,5R)-2,8- Dioxabicyclo[3.3.0]octan-3-one from Its Enantiomer: A Subunit of Clerodane Derivatives

F. Petit, R. Furstoss*
  • *Groupe de Chimie Organique et Bioorganique, URA CNRS 1320 - Faculté des Sciences de Luminy, Case 901 - 163, Avenue de Luminy, F-13288 Marseille Cedex 9, France
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Publication Date:
31 December 2000 (online)

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The (1S,5R) enantiomer of 2,8-dioxabicyclo[3.3.0]octan-3-one has been prepared by a seven-step synthesis starting from its (1R,5S) antipode prepared by microbiologically mediated Baeyer-Villiger oxidation of the corresponding bicyclic precursor. This lactone constitutes a potentially valuable chiral building block for the synthesis of clerodane derivatives.

biocatalysis - Baeyer-Villiger oxidation - enantiopure clerodane subunit