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Total Synthesis of Eudesmanolides Alantolactone, Isoalantodiene, Alloalantolactone, and 5α,6α-Epoxyalantolactone

Year: 2025
Type: preprint
Abstract: We report a 13-step total synthesis of the sesquiterpenoid lactone alantolactone and the first total syntheses of isoalantodiene, alloalantolactone, and 5α,6α-epoxyalantolactone. Key steps feature the intramolecular Diels–Alder cycloaddition of furan with an unactivated 1,1-disubstituted alkene to establish a quaternary carbon center, a palladium-catalyzed α-alkenylation of ketene silyl acetals, and a strain-promoted isomerization of a complex oxabicycle. We also describe the first enantioselective approach to this class of natural products.
Source: ChemRxiv
DOI: 10.26434/chemrxiv-2025-694w3
Authors: Julio Manuel Larach, Justin D DeBow, Sarosh Abraham, Anthony J Stevens, Veronica Carta, Kevin GM Kou
Language: English
Subfield: Cancer Research
Open Access status: green
Funders: National Science Foundation, U.S. Department of Education, Pfizer, National Institutes of Health, Directorate for Mathematical and Physical Sciences, National Institute of General Medical Sciences, Division of Chemistry
Awards: G141851601, G3113786527, MRI: Acquisition of a Hybrid Supercritical Chromatography, High-Pressure Chromatograph, Quadrupole-Time-of-Flight Mass Spectrometer (SFC/UHPLC Q-ToF/MS), G5560904802, G5986892838, G6671297155, G7667766050, CAREER: Innovating Oxidative C–H Functionalization via Rhodium and Cobalt Catalysis, G8839305273, G9000158980
OpenAlex ID: W4413811722
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