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  • Efficient synthesis of the structural core of tetracyclines by a palladium-catalyzed domino Tsuji-Trost-Heck-Mizoroki reaction.

Efficient synthesis of the structural core of tetracyclines by a palladium-catalyzed domino Tsuji-Trost-Heck-Mizoroki reaction.

Chemistry (Weinheim an der Bergstrasse, Germany) (2008-01-18)
Lutz F Tietze, Thomas Redert, Hubertus P Bell, Sascha Hellkamp, Laura M Levy
PMID18200642
ABSTRACT

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.