Synthesis of Optically Active 7-Oxabicyclo[2.2.1]heptanes and Assignment of Absolute Configuration

Jagabandhu Das; Martin F. Haslanger; J. Z. Gougoutas; Mary F. Malley

doi:10.1055/s-1987-28183

Synthesis 1987; 1987(12): 1100-1103
DOI: 10.1055/s-1987-28183

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Synthesis of Optically Active 7-Oxabicyclo[2.2.1]heptanes and Assignment of Absolute Configuration

Jagabandhu Das^* , Martin F. Haslanger, J. Z. Gougoutas, Mary F. Malley

^*The Squibb Institute for Medical Research, P.O. Box 4000, Princeton, NJ 08543-4000, U.S.A.

Abstract

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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.

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