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

Citation

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

Abstract

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.

Item Type:Thesis (Dissertation (Ph.D.))
Subject Keywords:Chemistry
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemistry
Thesis Availability:Public (worldwide access)
Research Advisor(s):
  • Ireland, Robert E.
Thesis Committee:
  • Grubbs, Robert H. (chair)
  • Dervan, Peter B.
  • Richards, John H.
  • Dougherty, Dennis A.
  • Ireland, Robert E.
Defense Date:2 May 1986
Other Numbering System:
Other Numbering System NameOther Numbering System ID
UMI8623962
Funders:
Funding AgencyGrant Number
Phi Kappa PhiUNSPECIFIED
ARCS FoundationUNSPECIFIED
CaltechUNSPECIFIED
Record Number:CaltechTHESIS:11082019-144704211
Persistent URL:https://resolver.caltech.edu/CaltechTHESIS:11082019-144704211
DOI:10.7907/rne7-j668
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:11905
Collection:CaltechTHESIS
Deposited By: Melissa Ray
Deposited On:08 Nov 2019 23:15
Last Modified:16 Apr 2021 23:25

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