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
  • Degree
    Doctor of Philosophy
  • DOI
  • License
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