Approach to the Synthesis of the Acyltetramic Acid Antibiotic Bu-2313

• Main Author: Wardle, Robert Budge
• Format: Others
• Language: en
• Published: 1986
• Online Access: https://thesis.library.caltech.edu/11905/1/wardle-rb-1986.pdf; Wardle, Robert Budge (1986) Approach to the Synthesis of the Acyltetramic Acid Antibiotic Bu-2313. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/rne7-j668. https://resolver.caltech.edu/CaltechTHESIS:11082019-144704211 <https://resolver.caltech.edu/CaltechTHESIS:11082019-144704211>

<p>An approach to the synthesis of the bicyclononane portion of the 3-acyltetramic acid antibiotic Bu-2313 is presented. The highly unstable α-ketoaldehyde obtained by Swern oxidation of the diol 30 was allowed to condense with the unreactive α-ketophosphoranylidene 18 affording the enedione 31. The silyl ether was cleaved and the hydroxyl caused to add to the enedione in a five-exo fashion to form the tetrahydrofuran. The combination of functional groups necessary for ketal formation was investigated showing that the system does not form the desired ketal in most circumstances (Table I). Given the correct functional group array, it was shown that the ketalization is more favorable with the stereochemistry of the natural product.</p>