Total synthesis of two isoflavone C-glycosides (6-tert-butyl puerarin and 6-tert-butyl-4′-methoxypuerarin) through the deoxybenzoin pathway

Add time:08/21/2019    Source:sciencedirect.com

The total synthesis of two isoflavone C-glycosides (6-tert-butylpuerarin and 6-tert-butyl-4′-methoxypuerarin) was achieved through the deoxybenzoin pathway with overall yields of 14.6% and 14.2%. The key intermediate 12 was obtained by de-tert-butylation of 10 with trifluoroacetic acid and Friedel-Crafts acetylation of 2-C-β-d-glucopyranoside 11. The ring closure of 12 with the POCl3/DMF reagent resulted glucosyl isoflavone formation 13, which was debenzylated and demethylated by BBr3 to obtain 14 and 15. This pathway represents a novel synthetic pathway based on Friedel-Crafts acetylation and Vilsmeier-Haack cyclization to achieve isoflavone C-glycosides in high yields.

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