<p dir="ltr">Dihydro-β-agarofurans are a class of polyester sesquiterpene secondary metabolites isolated from the <i>Celastraceae</i> plant family. Many compounds in this class have demonstrated biological activity and have therefore generated much synthetic interest. However, their <i>trans</i>-decalin/tetrahydrofuranyl ring system and high levels of oxidation make them synthetically challenging. The first chapter presents a discussion on the biological activity and various historical methods used to construct this ring system. The second chapter describes the new dearomative oxidation/cyclization method developed by our group to rapidly synthesize the tricyclic ring system in only 9 steps from commercially available 6-methoxy-1-tetralone. Other key steps include a MHAT reduction of a b,b-disubstituted dienone, stereospecific reduction of an enone, and hydroxyl-directed Simmons-Smith cyclopropanation. The large-scale synthesis of these advanced synthetic intermediates and the attempted elaboration to the dihydro-β-agarofuran core is described in detail.</p>
| Identifer | oai:union.ndltd.org:purdue.edu/oai:figshare.com:article/26264330 |
| Date | 13 July 2024 |
| Creators | Andrew Lancaster Caskey (19109156) |
| Source Sets | Purdue University |
| Detected Language | English |
| Type | Text, Thesis |
| Rights | CC BY 4.0 |
| Relation | https://figshare.com/articles/thesis/_b_Progress_Towards_an_Expedient_Synthesis_of_the_Core_of_Dihydro-_-agarofuran_Natural_Products_b_/26264330 |
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