Total synthesis of puerarin, an isoflavone C-glycoside |
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Authors: | David YW Lee Wu-Yan ZhangVishnu Vardhan R Karnati |
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Institution: | Bioorganic and Natural Products Laboratory, Harvard Medical School, McLean Hospital, 115 Mill Street, Belmont, MA 02478, USA |
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Abstract: | We completed the first total synthesis of puerarin (1), an isoflavone C-glycoside. The key intermediate, β-d-glucopyranosyl-2,6-dimethoxybenzene (9), was obtained by coupling of a lithiated aromatic reagent (3) with pyranolactone (2) in 56% yield. Condensation of (16) with p-methoxybenzaldehyde gave the chalcone (17). The protected chalcone (18) was cyclized to (19) in the presence of Tl(NO3)3. Demethylation of (19) was accomplished by refluxing with TMSI in CH3CN to give puerarin (1). |
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Keywords: | puerarin total synthesis natural product isoflavone C-glycoside |
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