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Generation of three stereogenic centers in the angular tetracyclic framework of 3 is possible starting from enantiomerically pure naphthoquinone 1 and the substituted racemic vinylcyclohexene 2.The product 3 is formed in a one-pot domino reaction comprising Diels–Alder cycloaddition and pyrolytic elimination of the sulfoxide. The key step is the kinetic resolution of the racemic diene.
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Carreño et al. (1997) studied this question.
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