Synthesis of CBD and Its Derivatives Bearing Various C4′-Side Chains with a Late-Stage Diversification Method
A novel synthetic route for making (−)-CBD and its derivatives bearing various C4′-side chains is developed by a late-stage diversification method. Starting from commercially available phloroglucinol, the key intermediate (−)-CBD-2OPiv-OTf is efficiently and regioselectively prepared and further und...
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Veröffentlicht in: | Journal of organic chemistry 2020-02, Vol.85 (4), p.2704-2715 |
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Hauptverfasser: | , , , , , , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | A novel synthetic route for making (−)-CBD and its derivatives bearing various C4′-side chains is developed by a late-stage diversification method. Starting from commercially available phloroglucinol, the key intermediate (−)-CBD-2OPiv-OTf is efficiently and regioselectively prepared and further undergoes Negishi cross-coupling to furnish (−)-CBD. This approach allowed an efficient synthesis of (−)-CBD in a five-step total 52% yield on a 10 g scale. Furthermore, diversification on the C4′-side chain with this method can be realized in a wide range. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.9b02880 |