<p>An original palladium-catalyzed
ring opening carbonylative lactonization of synthetic available
hydroxycyclopropanols was reported to efficiently synthesize tetrahydrofuran
(THF) and tetrahydropyran (THP)-fused bicyclic γ-lactones, two unique scaffolds
often found in quite a few natural products. This new developed reaction
features mild reaction conditions, good functional group tolerability, and the
scale-up abilities. The synthetic application was demonstrated in a short total
synthesis of (±)-Paeonilide. The THF-fused bicyclic γ-lactone products can be readily
diversified into some medicinally important structures, which further broadens
the application of this new carbonylation approach.</p>
<p>The first total synthesis of Phleghenrine A was reported. This synthesis
features an unprecedented inverse electron-demand Diels-Alder reaction and Tiffeneau-Demjanov
ring expansion to rapidly construct bicyclo[3,2,2]-nonane core structure of
Phleghenrine alkaloids. Two Diels-Alder adducts were synthesized, which were
the synthetic precursors for divergent synthesis of Phleghenrine A and B,
respectively.</p>
| Identifer | oai:union.ndltd.org:purdue.edu/oai:figshare.com:article/15078792 |
| Date | 29 July 2021 |
| Creators | Xinpei Cai (11205603) |
| Source Sets | Purdue University |
| Detected Language | English |
| Type | Text, Thesis |
| Rights | CC BY 4.0 |
| Relation | https://figshare.com/articles/thesis/PALLADIUM-CATALYZED_HYDROXYCYCLOPROPANOL_RING-OPENING_CARBONYLATIVE_LACTONIZATION_TO_FUSED_BICYCLIC_LACTONES_AND_TOTAL_SYNTHESIS_OF_PHLEGHENRINE_ALKALOIDS/15078792 |
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