Worldwide, there are plants known as psychoactive plants that naturally contain psychedelic active components. They have a high concentration of neuroprotective substances that can interact with the nervous system to produce psychedelic effects. Despite these plants' hazardous potential, recreational use of them is on the rise because of their psychoactive properties. Early neuroscience studies relied heavily on psychoactive plants and plant natural products (NPs), and both recreational and hazardous NPs have contributed significantly to the understanding of almost all neurotransmitter systems. Worldwide, there are many plants that contain psychoactive properties, and people have been using them for ages. Psychoactive plant compounds may significantly alter how people perceive the world.
1. Org Lett. 2024 Jan 26;26(3):625-630. doi: 10.1021/acs.orglett.3c03942. Epub 2024 Jan 11. Copper/Iodine Co-catalyzed Oxygenative Transannulation of Tryptamines Enables Direct Synthesis of Donaxaridine and Its Derivatives. Sun YZ(1)(2), Wu YA(1)(2), Shi J(1)(2), Wu W(1)(2), Song JR(1)(2), Ren H(1)(2). Author information: (1)State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang 550014, P. R. China. (2)Natural Products Research Center of Guizhou Province, Guiyang 550014, P. R. China. We report a general copper/iodine co-catalyzed oxygenative transannulation strategy using readily available tryptamines. Molecular oxygen and water are used as oxygen sources and provide direct access to the donaxaridine scaffold and its derivatives. This methodology is applied to the efficient synthesis of the natural products donaxaridine, chimonamidine, donaxanine, donaxarine, and aline in just one or two steps. The tryptamines, albeit with oxy-sensitive dialkyl N-H groups, are selectively oxidized through a single-electron transfer dioxygenation process. DOI: 10.1021/acs.orglett.3c03942 PMID: 38206574 2. Angew Chem Int Ed Engl. 2023 Dec 18;62(51):e202313687. doi: 10.1002/anie.202313687. Epub 2023 Nov 22. Copper-Catalyzed Oxygenative Skeletal Rearrangement of Tetrahydro-β-carbolines Using H(2) O and O(2) as Oxygen Sources. Peng YS(1)(2), Wang W(3), Shi J(1)(2), Wu W(1)(2), Song JR(1)(2), Pan WD(1)(2), Hao GF(3), Ren H(1)(2). Author information: (1)State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, 550014, Guiyang, P. R. China. (2)Natural Products Research Center of Guizhou Province, 550014, Guiyang, P. R. China. (3)National Key Laboratory of Green Pesticide, State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, 550025, Guiyang, P. R. China. Herein, we report an unprecedented skeletal rearrangement reaction of tetrahydro-β-carbolines enabled by copper-catalyzed single-electron oxidative oxygenation, in which H2 O and O2 act as oxygen sources to generate a unique 2-hydroxyl-3-peroxide indoline intermediate. The synthetic reactivity of 2-hydroxyl-3-peroxide indoline species was demonstrated by a unique multi-step bond cleavage and formation cascade. Using a readily available copper catalyst under open-air conditions, highly important yet synthetically difficult spiro[pyrrolidone-(3,1-benzoxazine)] products were obtained in a single operation. The synthetic utility of this methodology is demonstrated by the efficient synthesis of the natural products donaxanine and chimonamidine, as well as the 3-hydroxyl-pyrroloindoline scaffold, in just one or two steps. © 2023 Wiley-VCH GmbH. DOI: 10.1002/anie.202313687 PMID: 37950324