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Use of Enantioselective Aldol Condensations: Efforts Directed Towards the Total Synthesis of Ionomycin

Citation

Shih, Thomas Loong (1984) Use of Enantioselective Aldol Condensations: Efforts Directed Towards the Total Synthesis of Ionomycin. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/vhx3-s283. https://resolver.caltech.edu/CaltechTHESIS:10192018-103740684

Abstract

The amino acid derived N-acyl oxazolidones were found to be excellent chiral enolate synthons in the aldol condensation. The dialkylboron enolates of these imides exhibit very high levels of asymmetric induction and diastereoselection. However, the use of N-acetyl oxazolidones resulted in much lower diastereoselection. In these cases, substitution of N-acetyl oxazolidones with N-α-thiomethylacetyl oxazolidones (followed by Raney Nickel desulfurization) restored the high level of stereoselection.

Application of this methodology to the total synthesis of ionomycin is described.

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):
  • Dougherty, Dennis A.
Thesis Committee:
  • Evans, David A. (chair)
  • Grubbs, Robert H.
  • Collins, Terrence J.
  • Dougherty, Dennis A.
Defense Date:18 November 1983
Record Number:CaltechTHESIS:10192018-103740684
Persistent URL:https://resolver.caltech.edu/CaltechTHESIS:10192018-103740684
DOI:10.7907/vhx3-s283
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:11237
Collection:CaltechTHESIS
Deposited By: Lisa Fischelis
Deposited On:22 Oct 2018 16:34
Last Modified:19 Apr 2021 22:27

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