Synthetic Transformation on Shikimic Acid.
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.
Document Details
- Document Type
- Technical Report
- Publication Date
- Mar 15, 1988
- Accession Number
- ADA195400
Entities
People
- Edward D. White Iii
Organizations
- Oregon State University