The Pd-catalyzed domino Tsuji-Trost-Heck-Mizoroki reactions of compounds 18, 27, and 34, respectively, each containing an allyl acetate and a halogen aryl moiety, lead to the formation of hexahydronaphthacenes 2 and 3 and octahydroanthracene 4 in 62-81 % yield. The octahydroanthracene and hexahydronaphthacene motifs are found in many natural products, for example, the tetracycline antibiotics.
Antibiotics U 1200 Efficient Synthesis of the Structural Core of Tetracyclines by a Palladium-Catalyzed Domino Tsuji-Trost-Heck-Mizoroki Reaction. -The reaction is a powerful tool for the efficient preparation of substituted octahydroanthracenes and hexahydronaphthacenes. -(TIETZE*, L. F.; REDERT, T.; BELL, H. P.; HELLKAMP, S.; LEVY, L. M.; Chem. Eur.
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