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A General Route to meta-(Arylsulfanyl) and meta-(Alkylsulfanyl) Substituted Phenols and Synthetic Studies on Sorbicillactones A and B

  • Author / Creator
    Do, Nhan Van Thanh
  • Chapter 1 describes a general route for making meta-(arylsulfanyl) and meta-(alkylsulfanyl) phenols using DBU assisted aromatization developed in this laboratory. Thismethod is general and enables the construction of the C-S bond without using high temperatures or transition metal catalyst. The method involves O-tosylation of cyclohexane-1,3-dione,addition-elimination of a thiolate and bromination at C-2 of the resulting 3-arylsulfanyl- or 3-alkylsulfanylcyclohex-2-en-1-one. Finally, treatment with DBU gives the 3-arylsulfanyl- or 3-alkylsulfanylphenol.Chapter 2 describes synthetic studies towards the total synthesis of sorbicillactones A and B. Several different approaches were explored to construct the challenging amide quaternary center in the 5-membered lactone ring. During these studies an intramolecular Michael addition was discovered. This key transformation allowed the construction of the carbocyclic core of sorbicillactone A and B in five steps with the correct stereochemistry at all of the stereogeniccenters, thus opening the door for the further transformations needed to reach the natural products.

  • Subjects / Keywords
  • Graduation date
    Spring 2022
  • Type of Item
    Thesis
  • Degree
    Doctor of Philosophy
  • DOI
    https://doi.org/10.7939/r3-nc6m-9t30
  • 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.