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

Organic letters (2012-06-05)
Simon Trosien, Siegfried R Waldvogel
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Molybdenum(V) chloride, 95%
Sigma-Aldrich
9,10-Phenanthrenequinone, 95%
Sigma-Aldrich
Molybdenum(V) chloride, anhydrous, powder, 99.99% trace metals basis (excluding W)
Sigma-Aldrich
9,10-Phenanthrenequinone, ≥99%

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