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Abstract The natural chalcone bavachromanol has been prepared through a tandem reaction sequence that joins cationic cyclization of an epoxide to an adjacent MOM-acetal with electrophilic aromatic substitution by a… Click to show full abstract
Abstract The natural chalcone bavachromanol has been prepared through a tandem reaction sequence that joins cationic cyclization of an epoxide to an adjacent MOM-acetal with electrophilic aromatic substitution by a presumed methoxymethylene cation. Only a single regioisomer of the tandem product was observed, with substitution taking place exclusively ortho to the position of the original acetal. This regiocontrol provided a key intermediate from a symmetrical precursor, and allowed preparation of the meroterpenoid through a short reaction sequence.
Journal Title: Tetrahedron Letters
Year Published: 2018
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