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Published on: June 18, 2020
Total Synthesis of Isodihydrokoumine, (19 Z)-Taberpsychine, and (4 R)-Isodihydroukoumine N4-Oxide
Jeff K Kerkovius1, Michael A Kerr1
1Department of Chemistry , University of Western Ontario , 1151 Richmond Street , London , ON N6A 3K7 , Canada.
Abstract:
We report the total synthesis of the natural products isodihydrokoumine and (19 Z)-taberpsychine in 11 steps each and (4 R)-isodihydrokoumine N4-oxide in 12 steps from commercially available starting materials. The key reactions include an intramolecular [3 + 2] nitrone cycloaddition and Lewis acid mediated cyclizations of a common intermediate to provide the core structures of either taberpsychine or isodihydrokoumine.
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