Continuous-Flow Synthesis of Δ(9)-Tetrahydrocannabinol and Δ(8)-Tetrahydrocannabinol from Cannabidiol

[Image: see text] A challenging step in the preparation of tetrahydrocannabinol analogs is an acid-catalyzed intramolecular cyclization of the cannabidiol precursor. This step typically affords a mixture of products, which requires extensive purification to obtain any pure products. We report the de...

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Autores principales: Bassetti, Benedetta, Hone, Christopher A., Kappe, C. Oliver
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10167683/
https://www.ncbi.nlm.nih.gov/pubmed/37014222
http://dx.doi.org/10.1021/acs.joc.3c00300
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author Bassetti, Benedetta
Hone, Christopher A.
Kappe, C. Oliver
author_facet Bassetti, Benedetta
Hone, Christopher A.
Kappe, C. Oliver
author_sort Bassetti, Benedetta
collection PubMed
description [Image: see text] A challenging step in the preparation of tetrahydrocannabinol analogs is an acid-catalyzed intramolecular cyclization of the cannabidiol precursor. This step typically affords a mixture of products, which requires extensive purification to obtain any pure products. We report the development of two continuous-flow protocols for the preparation of (−)-trans-Δ(9)-tetrahydrocannabinol and (−)-trans-Δ(8)-tetrahydrocannabinol.
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spelling pubmed-101676832023-05-10 Continuous-Flow Synthesis of Δ(9)-Tetrahydrocannabinol and Δ(8)-Tetrahydrocannabinol from Cannabidiol Bassetti, Benedetta Hone, Christopher A. Kappe, C. Oliver J Org Chem [Image: see text] A challenging step in the preparation of tetrahydrocannabinol analogs is an acid-catalyzed intramolecular cyclization of the cannabidiol precursor. This step typically affords a mixture of products, which requires extensive purification to obtain any pure products. We report the development of two continuous-flow protocols for the preparation of (−)-trans-Δ(9)-tetrahydrocannabinol and (−)-trans-Δ(8)-tetrahydrocannabinol. American Chemical Society 2023-04-04 /pmc/articles/PMC10167683/ /pubmed/37014222 http://dx.doi.org/10.1021/acs.joc.3c00300 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Bassetti, Benedetta
Hone, Christopher A.
Kappe, C. Oliver
Continuous-Flow Synthesis of Δ(9)-Tetrahydrocannabinol and Δ(8)-Tetrahydrocannabinol from Cannabidiol
title Continuous-Flow Synthesis of Δ(9)-Tetrahydrocannabinol and Δ(8)-Tetrahydrocannabinol from Cannabidiol
title_full Continuous-Flow Synthesis of Δ(9)-Tetrahydrocannabinol and Δ(8)-Tetrahydrocannabinol from Cannabidiol
title_fullStr Continuous-Flow Synthesis of Δ(9)-Tetrahydrocannabinol and Δ(8)-Tetrahydrocannabinol from Cannabidiol
title_full_unstemmed Continuous-Flow Synthesis of Δ(9)-Tetrahydrocannabinol and Δ(8)-Tetrahydrocannabinol from Cannabidiol
title_short Continuous-Flow Synthesis of Δ(9)-Tetrahydrocannabinol and Δ(8)-Tetrahydrocannabinol from Cannabidiol
title_sort continuous-flow synthesis of δ(9)-tetrahydrocannabinol and δ(8)-tetrahydrocannabinol from cannabidiol
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10167683/
https://www.ncbi.nlm.nih.gov/pubmed/37014222
http://dx.doi.org/10.1021/acs.joc.3c00300
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