Crossref Cited-by Linking logo

Collect. Czech. Chem. Commun. 2001, 66, 1257-1268
https://doi.org/10.1135/cccc20011257

Tetrahydrocannabinol Revisited: Synthetic Approaches Utilizing Molybdenum Catalysts

Andrei V. Malkov* and Pavel Kočovský*

Department of Chemistry, University of Glasgow, Glasgow G12 8QQ, U.K.

Crossref Cited-by Linking

  • Li Wen-Cong, Meng He, Ming Jialin, Chen Shufeng: Rhodium-Catalyzed Asymmetric Addition to 4- or 5-Carbonyl-cycloenones through Dynamic Kinetic Resolution: Enantioselective Synthesis of (−)-Cannabidiol. Org. Lett. 2024, 26, 1364. <https://doi.org/10.1021/acs.orglett.3c04281>
  • Abdel-Kader Maged S., Radwan Mohamed M., Metwaly Ahmed M., Eissa Ibrahim H., Hazekamp Arno, ElSohly Mahmoud A.: Chemistry and Pharmacology of Delta-8-Tetrahydrocannabinol. Molecules 2024, 29, 1249. <https://doi.org/10.3390/molecules29061249>
  • Masero Fabio, Mougel Victor: Molybdenum(iv) β-diketonate complexes as highly active catalysts for allylic substitution reactions. Chem. Commun. 2023, 59, 4636. <https://doi.org/10.1039/D3CC00572K>
  • Gurgone Lucía, La-Venia Agustina, Caprioglio Diego, Riveira Martín J.: Synthetic approaches to cis-THC, a promising scaffold in medicinal chemistry. Front. Nat. Prod. 2023, 2. <https://doi.org/10.3389/fntpr.2023.1225627>
  • Alfei Silvana, Schito Gian Carlo, Schito Anna Maria: Synthetic Pathways to Non-Psychotropic Phytocannabinoids as Promising Molecules to Develop Novel Antibiotics: A Review. Pharmaceutics 2023, 15, 1889. <https://doi.org/10.3390/pharmaceutics15071889>
  • Meehan-Atrash Jiries, Rahman Irfan: Novel Δ8-Tetrahydrocannabinol Vaporizers Contain Unlabeled Adulterants, Unintended Byproducts of Chemical Synthesis, and Heavy Metals. Chem. Res. Toxicol. 2022, 35, 73. <https://doi.org/10.1021/acs.chemrestox.1c00388>
  • Nguyen Gia-Nam, Jordan Erin Noel, Kayser Oliver: Synthetic Strategies for Rare Cannabinoids Derived from Cannabis sativa. J. Nat. Prod. 2022, 85, 1555. <https://doi.org/10.1021/acs.jnatprod.2c00155>
  • Quílez del Moral José F., Ruiz Martínez Cristina, Pérez del Pulgar Helena, Martín González Juan Eduardo, Fernández Ignacio, López-Pérez José Luis, Fernández-Arteaga Alejandro, Barrero Alejandro F.: Synthesis of Cannabinoids: “In Water” and “On Water” Approaches: Influence of SDS Micelles. J. Org. Chem. 2021, 86, 3344. <https://doi.org/10.1021/acs.joc.0c02698>
  • Giorgi Pascal D., Liautard Virginie, Pucheault Mathieu, Antoniotti Sylvain: Biomimetic Cannabinoid Synthesis Revisited: Batch and Flow All‐Catalytic Synthesis of (±)‐ortho‐Tetrahydrocannabinols and Analogues from Natural Feedstocks. Eur J Org Chem 2018, 2018, 1307. <https://doi.org/10.1002/ejoc.201800064>
  • Hanuš Lumír Ondřej, Meyer Stefan Martin, Muñoz Eduardo, Taglialatela-Scafati Orazio, Appendino Giovanni: Phytocannabinoids: a unified critical inventory. Nat. Prod. Rep. 2016, 33, 1357. <https://doi.org/10.1039/C6NP00074F>
  • Schafroth Michael A., Zuccarello Giuseppe, Krautwald Simon, Sarlah David, Carreira Erick M.: Stereodivergent Total Synthesis of Δ9‐Tetrahydrocannabinols. Angewandte Chemie 2014, 126, 14118. <https://doi.org/10.1002/ange.201408380>
  • Schafroth Michael A., Zuccarello Giuseppe, Krautwald Simon, Sarlah David, Carreira Erick M.: Stereodivergent Total Synthesis of Δ9‐Tetrahydrocannabinols. Angew Chem Int Ed 2014, 53, 13898. <https://doi.org/10.1002/anie.201408380>
  • Vece Vito, Ricci Jérémy, Poulain‐Martini Sophie, Nava Paola, Carissan Yannick, Humbel Stéphane, Duñach Elisabet: InIII‐Catalysed Tandem C–C and C–O Bond Formation between Phenols and Allylic Acetates. Eur J Org Chem 2010, 2010, 6239. <https://doi.org/10.1002/ejoc.201000738>
  • Yamamoto Yoshihiko, Itonaga Kouhei: Synthesis of Chromans via [3 + 3] Cyclocoupling of Phenols with Allylic Alcohols Using a Mo/o-Chloranil Catalyst System. Org. Lett. 2009, 11, 717. <https://doi.org/10.1021/ol802800s>
  • Yamamoto Yoshihiko, Itonaga Kouhei: Versatile Friedel–Crafts‐Type Alkylation of Benzene Derivatives Using a Molybdenum Complex/ortho‐Chloranil Catalytic System. Chemistry A European J 2008, 14, 10705. <https://doi.org/10.1002/chem.200801105>
  • Le Nôtre Jérôme, Martinez Ana Acosta, Dixneuf Pierre H, Bruneau Christian: Synthesis of new terpene derivatives via ruthenium catalysis: rearrangement of silylated enynes derived from terpenoids. Tetrahedron 2003, 59, 9425. <https://doi.org/10.1016/j.tet.2003.09.073>
  • Malkov Andrei V., Kocovsky Pavel: ChemInform Abstract: Tetrahydrocannabinol Revisited: Synthetic Approaches Utilizing Molybdenum Catalysts. ChemInform 2002, 33. <https://doi.org/10.1002/chin.200207176>
  • Fairlamb Ian J. S.: 3  Transition metals in organic synthesis : Part (i) Catalytic applications. Annu. Rep. Prog. Chem., Sect. B: Org. Chem. 2002, 98, 123. <https://doi.org/10.1039/B111464F>
  • Malkov Andrei V., Farn Benjamin P., Hussain Nigel, Kočovský Pavel: Molybdenum-Catalyzed Allylic Substitution in Glycals: A C-C Bond-Forming Ferrier-Type Reaction. Collect. Czech. Chem. Commun. 2001, 66, 1735. <https://doi.org/10.1135/cccc20011735>