Journal article
Synthesis of bavachromanol from resorcinol via a tandem cationic cascade/EAS sequence
Tetrahedron letters, Vol.59(14), pp.1363-1365
04/04/2018
DOI: 10.1016/j.tetlet.2018.02.041
Abstract
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•A tandem reaction sequence converts a symmetrical resorcinol derivative to a single bicyclic substitution product.•Only a single regioisomer of the tandem cyclization/EAS product was observed.•The meroterpenoid bavachromanol has been prepared in 9 steps and 7% yield.
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.
Details
- Title: Subtitle
- Synthesis of bavachromanol from resorcinol via a tandem cationic cascade/EAS sequence
- Creators
- Parin A ShahDavid F Wiemer
- Resource Type
- Journal article
- Publication Details
- Tetrahedron letters, Vol.59(14), pp.1363-1365
- Publisher
- Elsevier Ltd
- DOI
- 10.1016/j.tetlet.2018.02.041
- ISSN
- 0040-4039
- eISSN
- 1873-3581
- Language
- English
- Date published
- 04/04/2018
- Academic Unit
- Neuroscience and Pharmacology; Chemistry
- Record Identifier
- 9984216603502771
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