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Efficient Synthesis of the Structural Core of Tetracyclines by a Palladium‐Catalyzed Domino Tsuji–Trost–Heck–Mizoroki Reaction
Author(s) -
Tietze Lutz F.,
Redert Thomas,
Bell Hubertus P.,
Hellkamp Sascha,
Levy Laura M.
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200701676
Subject(s) - chemistry , palladium , moiety , domino , catalysis , heck reaction , aryl , yield (engineering) , organic chemistry , combinatorial chemistry , materials science , alkyl , metallurgy
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.