An enantiodivergent synthesis of the bicyclo[2.2.1]heptane lactone (2) is described, by regioselective reduction of the Diels–Alder adducts (3) and (4) with di-isobutylaluminium hydride followed by reductive elimination of the chiral auxiliary, 10-mercaptoisoborneol (9) through reaction with samarium(II) iodide.
Y. Arai, M. Matsui and T. Koizumi, J. Chem. Soc., Perkin Trans. 1, 1990, 1233 DOI: 10.1039/P19900001233
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