Synthetic transformations on shikimic acid
White, Edward D.
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Four strategies which involve synthetic elaboration of the shikimate nucleus are discussed. Methyl shikimate was differentially protected as the 3,4-0-cyclopentylidene ketal and as the 5-0-tert-butyldiphenylsilyl ether. The methyl ester was then reduced with diisobutylaluminum hydride and the resulting allylic alcohol was oxidized to aldehyde with pyridinium chlorochromate. The cyclopentylidene protecting group was removed to liberate the 3- and 4- hydroxyl groups which were acylated with maleic anhydride and succinic anhydride. The acylated aldehydes, as well as aldehyde were converted to their respective dimethlhydrazones