One-flow synthesis of tetrahydrocannabinol and cannabidiol using homo- and heterogeneous Lewis acids

Victor R.L.J. Bloemendal; Bram Spierenburg; Thomas J. Boltje; Jan C.M. van Hest; Floris P.J.T. Rutjes

doi:10.1007/s41981-020-00133-2

One-flow synthesis of tetrahydrocannabinol and cannabidiol using homo- and heterogeneous Lewis acids

Victor R.L.J. Bloemendal, Bram Spierenburg, Thomas J. Boltje, Jan C.M. van Hest, Floris P.J.T. Rutjes (Corresponding author)

Research output: Contribution to journal › Article › Academic › peer-review

9 Citations (Scopus)

Abstract

Continuous flow chemistry holds great potential for the production of biologically relevant molecules. Herein, we present an approach for the continuous synthesis of cannabidiol and tetrahydrocannabinol in a one-flow system. The designed route consists of a reaction cascade involving Friedel-Crafts alkylation, subsequent ring opening and cyclisation in up to 45% yield. The reactions were successfully performed using both hetero- and homogeneous Lewis acids in continuous flow and provide yields that are similar to comparable batch processes. Graphical abstract: [Figure not available: see fulltext.]

Original language	English
Pages (from-to)	99-105
Number of pages	7
Journal	Journal of Flow Chemistry
Volume	11
Issue number	2
Early online date	4 Jan 2021
DOIs	https://doi.org/10.1007/s41981-020-00133-2
Publication status	Published - Jun 2021

Funding

We kindly acknowledge funding by the H2020-FETOPEN-2016-2017 programme of the European Commission (Grant agreement number: 737266-ONE FLOW).

Funders	Funder number
European Union's Horizon 2020 - Research and Innovation Framework Programme	737266
H2020 European Research Council
European Commission

Keywords

Cannabinoids
Flow chemistry
Heterocycles
Heterogeneous Lewis acid catalysis

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10.1007/s41981-020-00133-2

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abstract = "Continuous flow chemistry holds great potential for the production of biologically relevant molecules. Herein, we present an approach for the continuous synthesis of cannabidiol and tetrahydrocannabinol in a one-flow system. The designed route consists of a reaction cascade involving Friedel-Crafts alkylation, subsequent ring opening and cyclisation in up to 45% yield. The reactions were successfully performed using both hetero- and homogeneous Lewis acids in continuous flow and provide yields that are similar to comparable batch processes. Graphical abstract: [Figure not available: see fulltext.]",

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AU - Bloemendal, Victor R.L.J.

AU - Spierenburg, Bram

AU - Boltje, Thomas J.

AU - van Hest, Jan C.M.

AU - Rutjes, Floris P.J.T.

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AB - Continuous flow chemistry holds great potential for the production of biologically relevant molecules. Herein, we present an approach for the continuous synthesis of cannabidiol and tetrahydrocannabinol in a one-flow system. The designed route consists of a reaction cascade involving Friedel-Crafts alkylation, subsequent ring opening and cyclisation in up to 45% yield. The reactions were successfully performed using both hetero- and homogeneous Lewis acids in continuous flow and provide yields that are similar to comparable batch processes. Graphical abstract: [Figure not available: see fulltext.]

KW - Cannabinoids

KW - Flow chemistry

KW - Heterocycles

KW - Heterogeneous Lewis acid catalysis

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One-flow synthesis of tetrahydrocannabinol and cannabidiol using homo- and heterogeneous Lewis acids

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