A general route to 1,3'-bipyrroles, conversion of cyclohexenone-type systems into phenols and synthetic studies on Coleophomone B

• Author / Creator

  Shao, Wenjie

• Chapter 1 describes a general route for making 1,3'-bipyrroles. This work involves intermolecular conjugate displacement using a special Michael acceptor developed in this laboratory. This method is general and enables the construction of highly substituted 1,3'-bipyrroles. The route was first employed to carry out the total synthesis of Marinopyrrole B by previous laboratory members. Chapter 2 describes a new family of routes to substituted phenols, including meta-substituted phenols, which was discovered during studies on the total synthesis of coleophomone B. This work enables efficient aromatization of 2-bromocyclohex-2-en-1-ones to phenols under very mild conditions. The method has extraordinary broad substrate scope and it is transition-metal free. Chapter 3 describes synthetic studies towards the total synthesis of coleophomone B. Several different approaches were explored to construct the challenging tricarbonyl system and the strained 11-membered macrocycle. Although the macrocyclization was not achieved, several advanced precursors for cyclization were synthesized and a new aromatization was discovered.

• Subjects / Keywords

  • Bipyrrole
  • Phenol
  • Coleophomone B

• Graduation date

  Fall 2016

• Type of Item

  Thesis

• Degree

  Doctor of Philosophy

• DOI

  https://doi.org/10.7939/R3KP7V616

• 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.