Synthesis of highly functionalized 9,10-phenanthrenequinones by oxidative coupling using MoCl5.
The strong oxidative power of molybdenum pentachloride gives rise to an efficient oxidative C-C bond formation of benzil derivatives to the corresponding 9,10-phenanthrenequinones. A highly complementary method to previous approaches was developed. The required derivatives are accessible in a modular fashion and in excellent yields. By this approach the orchid-derived natural product cypripediquinone A was synthesized for the first time.
Institute of Organic Chemistry, Duesbergweg 10-14, Johannes Gutenberg-University Mainz, 55128 Mainz, Germany.
Simon
S
Trosien
Siegfried R
SR
Waldvogel
D002712:Chlorides / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D008982:Molybdenum / Q000737:chemistry*; D058451:Oxidative Coupling; D010616:Phenanthrenes / Q000138:chemical synthesis*
D002712:Chlorides; D010616:Phenanthrenes; C005399:9,10-phenanthrenequinone; D008982:Molybdenum; C085192:molybdenum chloride