First Synthesis of Bioactive Diphyllin Glycosides Isolated from Justicia patentiflor Hemsl
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摘要:
The syntheses of three naturally occurring diphyllin glycosides have been achieved. 7-O-β-D-Quinovopyranosyldiphyllin (patentiflorin A) and 7-O-β-L-fucopyranosyldiphyllin (patentiflorin B) were synthesized by the glycosylation of diphyllin with peracetylglycosyl bromides under phase transfer catalysis (PTC) conditions.4"-O-Acetyl-7-O-β-L-fucopyranosyldiphyllin (4"-O-acetyl patentiflorin B) was obtained from patentiflorin B on an orthoesterification-orthoester rearrangement approach. Their 1H NMR, 13C NMR and HRMS signals are all consistent with those reported for the natural product.