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Synthetic Access to Cannabidiol and Analogs as Active Pharmaceutical Ingredients
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    Synthetic Access to Cannabidiol and Analogs as Active Pharmaceutical Ingredients
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    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 2020, 63, 21, 12131–12136
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    https://doi.org/10.1021/acs.jmedchem.0c00095
    Published June 12, 2020
    Copyright © 2020 American Chemical Society

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    Cannabinoids have surely been one of the most widely self-administered drugs other than caffeine. The U.S. FDA recently approved one cannabinoid-based drug whose active pharmaceutical ingredient (API) is cannabidiol (CBD). The long history of individual use of cannabis for a wide range of conditions has sparked great interest in other uses of CBD, in ethical drugs and botanical supplements as well as in foods and nonprescription wellness products. CBD may be sourced from cannabis plants but can also be prepared synthetically, the topic of this review.

    Copyright © 2020 American Chemical Society

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    This article is cited by 24 publications.

    1. Yann Pauvert, André B. Charette. Asymmetric Synthesis of (−)-Cannabidiol (CBD), (−)-Δ9-Tetrahydrocannabinol (Δ9-THC) and Their cis Analogs Using an Enantioselective Organocatalyzed Diels–Alder Reaction. Organic Letters 2024, 26 (29) , 6081-6085. https://doi.org/10.1021/acs.orglett.4c01622
    2. Wen-Cong Li, He Meng, Jialin Ming, Shufeng Chen. Rhodium-Catalyzed Asymmetric Addition to 4- or 5-Carbonyl-cycloenones through Dynamic Kinetic Resolution: Enantioselective Synthesis of (−)-Cannabidiol. Organic Letters 2024, 26 (7) , 1364-1369. https://doi.org/10.1021/acs.orglett.3c04281
    3. Alexandra M. Millimaci, Richard V. Trilles, James H. McNeely, Lauren E. Brown, Aaron B. Beeler, John A. Porco, Jr.. Synthesis of Neocannabinoids Using Controlled Friedel–Crafts Reactions. The Journal of Organic Chemistry 2023, 88 (18) , 13135-13141. https://doi.org/10.1021/acs.joc.3c01362
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    12. Shanfang Fang, Wen-Tyng Kang, Haizhou Li, Qiongna Cai, Wanxin Liang, Minghui Zeng, Qian Yu, Rongcui Zhong, Yiwen Tao, Shouping Liu, Shuimu Lin. Development of cannabidiol derivatives as potent broad-spectrum antibacterial agents with membrane-disruptive mechanism. European Journal of Medicinal Chemistry 2024, 266 , 116149. https://doi.org/10.1016/j.ejmech.2024.116149
    13. Aguo Cheng, Suohui Zhang, Fanda Meng, Mengzhen Xing, Han Liu, Guozhong Yang, Yunhua Gao. Nanosuspension-Loaded Dissolving Microneedle Patches for Enhanced Transdermal Delivery of a Highly Lipophilic Cannabidiol. International Journal of Nanomedicine 2024, Volume 19 , 4061-4079. https://doi.org/10.2147/IJN.S452207
    14. Xiuli Wang, Huanbang Zhang, Yan Liu, Yang Xu, Bingyou Yang, Hua Li, Lixia Chen. An overview on synthetic and biological activities of cannabidiol (CBD) and its derivatives. Bioorganic Chemistry 2023, 140 , 106810. https://doi.org/10.1016/j.bioorg.2023.106810
    15. Eleana Lopušanskaja, Anne Paju, Ivar Järving, Margus Lopp. A direct alkylation of resorcinols. Synthetic Communications 2023, 53 (15) , 1216-1226. https://doi.org/10.1080/00397911.2023.2214645
    16. Guanghui Tang, Ying‐Jie Lim, Wei Wang, Zi Ye, Chong‐Jing Zhang, Shao Q. Yao. Orthogonal Strategies for Profiling Potential Cellular Targets of Anandamide and Cannabidiol. Chemistry – A European Journal 2023, 29 (43) https://doi.org/10.1002/chem.202300682
    17. Beatriz P. Ferreira, Gustavo Costa, Filipa Mascarenhas-Melo, Patrícia C. Pires, Fariba Heidarizadeh, Prabhanjan S. Giram, Priscila Gava Mazzola, Célia Cabral, Francisco Veiga, Ana Cláudia Paiva-Santos. Skin applications of cannabidiol: sources, effects, delivery systems, marketed formulations and safety. Phytochemistry Reviews 2023, 22 (3) , 781-828. https://doi.org/10.1007/s11101-023-09860-5
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    19. Susan Miller, Walter Moos, Barbara Munk, Stephen Munk, Charles Hart, David Spellmeyer. Backgrounder—Part 2. 2023, 27-64. https://doi.org/10.1016/B978-0-12-824304-6.00010-9
    20. Dorota Chelminiak-Dudkiewicz, Aleksander Smolarkiewicz-Wyczachowski, Kinga Mylkie, Magdalena Wujak, Dariusz T. Mlynarczyk, Pawel Nowak, Szymon Bocian, Tomasz Goslinski, Marta Ziegler-Borowska. Chitosan-based films with cannabis oil as a base material for wound dressing application. Scientific Reports 2022, 12 (1) https://doi.org/10.1038/s41598-022-23506-0
    21. Alice Maiocchi, Jacopo Barbieri, Valerio Fasano, Daniele Passarella. Stereoselective Synthetic Strategies to (−)‐Cannabidiol. ChemistrySelect 2022, 7 (28) https://doi.org/10.1002/slct.202202400
    22. Zi-Yi Huang, Min-Ru Jiao, Xiu Gu, Zi-Ran Zhai, Jian-Qi Li, Qing-Wei Zhang. Asymmetric Synthesis of 1,2-Limonene Epoxides by Jacobsen Epoxidation. Pharmaceutical Fronts 2021, 03 (03) , e113-e118. https://doi.org/10.1055/s-0041-1740241
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    24. Alexandra E. Golliher, Antonio J. Tenorio, Nina O. Dimauro, Nicolas R. Mairata, F. Omar Holguin, William Maio. Using (+)-carvone to access novel derivatives of (+)-ent-cannabidiol: The first asymmetric syntheses of (+)-ent-CBDP and (+)-ent-CBDV. Tetrahedron Letters 2021, 67 , 152891. https://doi.org/10.1016/j.tetlet.2021.152891

    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 2020, 63, 21, 12131–12136
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.jmedchem.0c00095
    Published June 12, 2020
    Copyright © 2020 American Chemical Society

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