Synthesis of Optically Active 7-Oxabicyclo[2.2.1]heptanes and Assignment of Absolute Configuration
- 1 January 1987
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1987 (12) , 1100-1103
- https://doi.org/10.1055/s-1987-28183
Abstract
The synthesis of optically active 7-oxabicyclo[2.2.1]heptane derivatives is described. The synthetic route requires the conversion of prochiral 7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride (2) to an easily separable mixture of diastereoisomeric acid-esters 3 and 5. Each of the pure diastereoisomers is obtained by use of the commercially available optical antipodes of menthol. Diastereoisomerically pure acid-esters 3 and 5 are separately transformed to enantiomerically pure lactones (+)- 1 and (-)-1 (ee > 98%). Lactone (+)-1 is converted to a d-menthyl acetal 8a and its absolute configuration is determined by X-ray analysis.Keywords
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