Accession Number : ADA195400

Title :   Synthetic Transformation on Shikimic Acid.

Descriptive Note : Master's thesis,

Corporate Author : OREGON STATE UNIV CORVALLIS

Personal Author(s) : White, Edward D , III

PDF Url : ADA195400

Report Date : 15 Mar 1988

Pagination or Media Count : 97

Abstract : 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.

Descriptors :   *ESTERS, *METHYL RADICALS, *SUCCINIC ACID, ANHYDRIDES, HYDROXYL RADICALS, OXIDATION, STRATEGY, TRANSFORMATIONS

Subject Categories : Organic Chemistry

Distribution Statement : APPROVED FOR PUBLIC RELEASE