Total Synthesis of (+)-Ipalbidine and Synthetic Studies on (+)-Sorbicillactone A

• Author / Creator

  Chea, JongMyoung

• Chapter 1 describes the total synthesis of (+)-ipalbidine. The indolizidine core structure was formed by use of an unusual 6-exo-trigonal radical cyclization as a key step. I started from the chiral pool using L-proline and obtained ipalbidine with an ee of >99.6%. Chapter 2 describes synthetic studies towards the total synthesis of sorbicillactone A. Most of the carbon skeleton of sorbicillactone A was assembled. However, the amination and methylation steps at C-3 remain to be accomplished. Several different approaches were explored to add stereoselectively the amino and methyl group at C-3. The most promising approach appears to be an unusual Claisen rearrangement that introduces two carbons at C-3 so constituted that they can be manipulated individually with one of them eventually being replaced by nitrogen.

• Subjects / Keywords

  • Total Synthesis of (+)-Ipalbidine and Synthetic Studies on (+)-Sorbicillactone A

• Graduation date

  Fall 2017

• Type of Item

  Thesis

• Degree

  Doctor of Philosophy

• DOI

  https://doi.org/10.7939/R33B5WQ7P

• License

  This thesis is made available by the University of Alberta Libraries with permission of the copyright owner solely for non-commercial purposes. This thesis, or any portion thereof, may not otherwise be copied or reproduced without the written consent of the copyright owner, except to the extent permitted by Canadian copyright law.