[reaction: see text]. A synthesis of a reduced version of the naphthazarin found in the rubromycin class of natural products is reported. The naphthalene ring system is formed via a Dötz reaction with a symmetrical alkyne. Differentiation between the C1' and C3' groups of the Dötz adduct is achieved by selective oxidation since the two methylene groups possess different oxidation potentials.
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Xie et al. (2001) studied this question.
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