Conversion of Cycloalk-2-en-1-ones into 2-Methylcycloalkane-1,3-diones and Formation of meta-Substituted Phenols

• Author / Creator

  Yu, Guojun

• The first chapter of this thesis describes the studies towards conversion of cycloalk-2-enones into 2-methylcyclo-alkane-1,3-diones. The key step is a Tamao–Fleming oxidation where a silyl group serves as a masked hydroxy group. Examination of various Tamao-Fleming procedures are discussed. In particular, mechanistic insight into the use of the Me3SiMe2Si unit is revealed. The second chapter describes studies aimed at the synthesis of meta-substituted phenols via transition metal-free aromatization. Based on the previous work from this laboratory, a general route to 3,5-disubstituted and polysubstituted phenols has been developed. Each of the substituents in the final aromatic product is installed in a completely region-controlled manner and each can have a wide range of values. A demonstration of this method in the synthesis of pharmaceutically important intermediates is described as well. Further application of this methodology towards the total synthesis of Fulvestrant (a breast cancer drug) is currently under investigation.

• Subjects / Keywords

  • transition-metal-free aromatization
  • meta-substituted phenols
  • Tamao–Fleming oxidation

• Graduation date

  Spring 2016

• Type of Item

  Thesis

• Degree

  Master of Science

• DOI

  https://doi.org/10.7939/R3MP4W42C

• 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.