Preparation of enantiomerically pure 2-(1′-aminomethyl)furan derivatives and synthesis of an unnatural polyhydroxylated piperidine |
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| Authors: | Xin Cong Ke-Gang Liu Zhu-Jun Yao |
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| Institution: | a Department of Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang Road, Nanjing 210009, China
b State Key Laboratory of Bioorganic and Natural Product Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China |
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| Abstract: | Zinc-mediated propargylation of α-acylaminoaldehydes, and subsequent oxidative isomerization followed by Ag(I)-catalyzed cycloisomerization conveniently provides a new enantioselective route to the corresponding 2-aminoalkylfurans. One of these furans was successfully converted into an unnatural polyhydroxylated piperidine that efficiently incorporated structural features of the starting material. This represents a new entrance to biologically interesting polyhydroxylated piperidines having diverse substitutions. |
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