Efficient synthesis of the structural core of tetracyclines by a palladium-catalyzed domino Tsuji-Trost-Heck-Mizoroki reaction.
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.
Tietze
Lutz F
LF
Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, Germany. ltietze@gwdg.de
Redert
Thomas
T
Bell
Hubertus P
HP
Hellkamp
Sascha
S
Levy
Laura M
LM
D001593:Benzyl Compounds / Q000737:chemistry; D002384:Catalysis; D004986:Ether / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013754:Tetracyclines / Q000138:chemical synthesis* / Q000737:chemistry
D001593:Benzyl Compounds; D013754:Tetracyclines; D004986:Ether; D010165:Palladium; C038682:benzyl bromide