Abstract:In this review, which covers the literature after 1998 we present new applications of D-(-)-Quinic acid where it has been successfully applied as chiral building block for the effective introduction a new stereogenic centers. Furthermore, examples are presented from complex natural products synthesis which also includes our own work.
A biomass‐based route to the preparation of hydroquinone starting from the renewable starting material quinic acid is described. Amberlyst‐15 in the dry form promoted the one‐step formation of hydroquinone from quinic acid in toluene without any oxidants or metal catalysts in 72 % yield. Several acidic polymer‐based resins and organic acids as promoters as well as a variety of reaction conditions were screened including temperature, concentration and low‐ and high‐boiling‐point solvents. A 1:4 (w/w) ratio of quinic acid/Amberlyst‐15 was determined to be optimal to promote hydroquinone formation with only traces of a dimeric side‐product. A mechanism has been proposed based on the decarbonylation of protonated quino‐1,5‐lactone that is supported by experimental and computational calculation data.
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