Total synthesis of puerarin, an isoflavone C-glycoside

DYW Lee, WY Zhang, VVR Karnati

Index: Lee, David Y. W.; Zhang, Wu-Yan; Karnati, Vishnu Vardhan R. Tetrahedron Letters, 2003 , vol. 44, # 36 p. 6857 - 6859

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Citation Number: 33

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 ...