U.v. irradiation of the cis bicyclic αβ-unsaturated ketone (5) in diethyl Lg-(+)-tartrate afforded a 1 : 7 mixture of the cis(5) and the trans ketone (6) enriched in the (–)-enantiomer; Wolff–Kishner reduction of (6) yielded (–)-D2-bicyclo[8.8.0]octadec-1(10)-ene (7)(optical purity 0·5–1·0%) with the (R)- configuration.
M. Nakazaki, K. Yamamoto and M. Maeda, J. Chem. Soc., Chem. Commun., 1980, 294 DOI: 10.1039/C39800000294
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