Organic Letters 2012-06-15

Synthesis of highly functionalized 9,10-phenanthrenequinones by oxidative coupling using MoCl5.

Simon Trosien, Siegfried R Waldvogel

Index: Org. Lett. 14(12) , 2976-9, (2012)

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Abstract

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.