American Chemical Society
ol8b01909_si_001.pdf (2.83 MB)

Lewis-Acid-Mediated Union of Epoxy-Carvone Diastereomers with Anisole Derivatives: Mechanistic Insight and Application to the Synthesis of Non-natural CBD Analogues

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journal contribution
posted on 2018-07-23, 11:20 authored by Sophia J. Bailey, Rishi R. Sapkota, Alexandra E. Golliher, Barry Dungan, Marat Talipov, F. Omar Holguin, William A. Maio
The use of trimethylsilyl trifluoro­methane­sulfonate as a mild means to unite epoxy-carvone silyl ethers with anisole derivatives to yield products that are structurally similar to the CBD scaffold is reported. Importantly, unlike related methods, this process can utilize both epoxy-carvone diastereomers and does not require the use of air/moisture-sensitive organometallic reagents. Several examples of aryl nucleophiles as well as mechanistic insight based on in silico computational analysis are presented.