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Synthesis of 8 hydroxy 7 12 dimethyl benz a anthracene and 11 hydroxy 7 12 dimethyl benz a anthracene tin ii chloride mediated reductions

Synthesis of 8 hydroxy 7 12 dimethyl benz a anthracene and 11 hydroxy 7 12 dimethyl benz a anthracene tin ii chloride mediated reductions

Journal of Organic Chemistry 45(12): 2301-2304

8-Methoxybenznthracene-7,12-dione (3) and 11-methoxybenznthracene-7,12-dione (4) were converted in high yields to the corresponding 7,12-bis(epoxides) (14a and 14b) (not isolated because of instability) by treatment with the ylide formed from trimethylsulfonium iodide. Reduction with lithium aluminum hydride afforded 7,12-dihydro-7,12-dihydroxy-8-methoxy-7,12-dimethylbenznthracene (5) and 7,12-dihydro-7,12-dihydroxy-11-methoxy-7,12-dimethylbenznthracene (6), respectively, in excellent yields.

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