The work disclosed in this dissertation outlines a newly discovered acidic alumina-mediated orthoallylation of unprotected phenols and the application of this method to the synthesis of prenylated
phenolic natural products including dorsmanin A and hyperbeanol Q.
Chapter 1 consists of a literature review of prenylated phenolic compounds and includes a
discussion of their biological significance followed by an extensive review of the various synthetic
strategies that have been used to prepare them. It is our intention to publish the content of this chapter
as a review article for the synthetic chemistry community.
Showcased in Chapter 2 is the optimization of a novel prenylation method via acidic alumina as the
promoter. Phenols and allyl alcohols are combined with acidic alumina in 1,2-dichloroethane or
acetonitrile to induce a proposed coordination of the substrates to the alumina surface via hydrogen
bonding which facilitates the regioselective ortho-prenylation of phenols. The extensive substrate
scope of this chemistry is discussed.
In Chapter 3, this alumina-mediated prenylation is applied to the syntheses of several
acylphloroglucinol natural products and unnatural structural analogues which are evaluated for their
antimicrobial and anthelmintic (anti-parasitic) activity. Some of these compounds exhibited
antimicrobial activity and some exhibited anthelmintic potential.
In Chapter 4, this prenylation strategy is further extended to the syntheses of additional prenylated
phenolic natural products: (±)-sanjuanolide and dorsmanin A. Investigations towards the synthesis of
HP1 are also reported. Development of the syntheses of these natural product targets provides a
useful venue to investigate the scope of our alumina-mediated phenol prenylation chemistry and to
identify its scope and limitations. / Thesis / Doctor of Philosophy (PhD)
| Identifer | oai:union.ndltd.org:mcmaster.ca/oai:macsphere.mcmaster.ca:11375/29239 |
| Date | January 2023 |
| Creators | Darveau, Patrick |
| Contributors | Magolan, Jakob, Chemistry and Chemical Biology |
| Source Sets | McMaster University |
| Language | English |
| Detected Language | English |
| Type | Thesis |
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