A Concise Synthesis of (2R,6R)-Hydroxynorketamine
Jianfeng Li1, Ankun Zhou2, Xiaoting Wang2
1School of Chinese Materia Medica and Yunnan Key Laboratory of Southern Medicinal Utilization, Yunnan University of Chinese Medicine, 1076 Yuhua Road, Chenggong District, Kunming 650500, Yunnan. P. R. of China.
Abstract:
A concise synthesis of (2R,6R)-hydroxynorketamine was accomplished in eight steps, starting from commercially available materials. This synthesis features a cerium chloride-enhanced Stork-Danheiser reaction, an asymmetric reduction of ketone by the Corey-Bakshi-Shibata reaction, a signature Overman rearrangement, and a facial selective dihydroxylation of an electronically deficient olefin by RuCl3/NaIO4. The overall yield is 7.3% with 94.5% ee.
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