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Divergent total synthesis reports the construction of enamine pyranonaphthoquinones, highlighting mechanistic insights.
A divergent total synthesis of enamine pyranonaphthoquinones BE-54238A and -B is described. This synthesis features (1) concise preparation of a pyrrolidine unit, (2) regioselective Friedel-Crafts reaction, and (3) biomimetic construction of the enamine pyranonaphthoquinone motif through imine formation and tautomerization. Mechanistic insight into the diastereoselectivity in the Friedel-Crafts reaction and the photolability of the pyrrolidinyl naphthoquinone were studied.
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Kawai et al. (2026) studied this question.
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