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. 2021 Sep 3;23(17):6836-6840. doi: 10.1021/acs.orglett.1c02393. Epub 2021 Aug 19. Total Synthesis of (-)-Picrinine, (-)-Scholarisine C, and (+)-5-β-Methoxyaspidophylline. Zou P(1), Yang H(1), Wei J(1), Wang T(1)(2), Zhai H(1)(2)(3). Author information: (1)The State Key Laboratory of Chemical Oncogenomics, Guangdong Provincial Key Laboratory of Nano-Micro Materials Research, School of Chemical Biology and Biotechnology, Shenzhen Graduate School of Peking University, Shenzhen 518055, China. (2)Institute of Marine Biomedicine, Shenzhen Polytechnic, Shenzhen 518055, China. (3)Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, China. The first asymmetric total synthesis of three picrinine-type akuammiline alkaloids, (-)-picrinine, (-)-scholarisine C, and (+)-5-β-methoxyaspidophylline, has been accomplished. The synthesis features an efficient acid-promoted oxo-bridge ring-opening and further carbonyl O-cyclization to assemble the furoindoline scaffold, an unusual Dauben-Michno oxidation to construct the requisite α,β-unsaturated aldehyde functionality, and a nickel-mediated reductive Heck reaction to forge the [3.3.1]-azabicyclic core. DOI: 10.1021/acs.orglett.1c02393 PMID: 34410141 [Indexed for MEDLINE] 2. Org Biomol Chem. 2019 Jul 17;17(28):6831-6842. doi: 10.1039/c9ob00855a. Total syntheses of several iridolactones and the putative structure of noriridoid scholarein A: an intramolecular Pauson-Khand reaction based one-stop synthetic solution. Salam A(1), Ray S(1), Zaid MA(1), Kumar D(1), Khan T(1). Author information: (1)Organic Synthesis Laboratory, School of Basic Sciences, Indian Institute of Technology Bhubaneswar, Khurdha-752050, Odisha, India. tabrez@iitbbs.ac.in. A simple and general approach towards the total syntheses of several iridolactones such as (±)-boschnialactone, (±)-7-epi-boschnialactone, (±)-teucriumlactone, (±)-iridomyrmecin, (±)-isoboonein, (±)-7-epi-argyol, (±)-scabrol A, (±)-7-epi-scabrol A, and (±)-patriscabrol as well as the putative structure of scholarein A is delineated. The synthetic strategy features a diastereoselective intramolecular Pauson-Khand reaction (IPKR) to construct the iridoid framework followed by some strategic synthetic manipulations to access the targeted monoterpenes including those having diverse oxy-functionalization patterns and with 3-5 contiguous stereogenic centres in a highly stereocontrolled manner. Also, the present endeavour includes the first total synthesis of scabrol A. DOI: 10.1039/c9ob00855a PMID: 31250873 [Indexed for MEDLINE] 3. Org Lett. 2017 Apr 7;19(7):1922-1925. doi: 10.1021/acs.orglett.7b00722. Epub 2017 Mar 30. Total Synthesis of Scholarisine K and Alstolactine A. Wang D(1), Hou M(1), Ji Y(1), Gao S(1). Author information: (1)Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University , 3663 N Zhongshan Road, Shanghai 200062, China. The first asymmetric total syntheses of scholarisine K and alstolactine A have been accomplished. Our syntheses feature (1) ring closure metathesis and an intramolecular Heck reaction to construct the 1,3-bridged [3,3,1] bicycle (C-D ring), (2) intramolecular alkylation followed by Fischer indolization to form the basic skeleton of akuammilines, and (3) bioinspired, acid-promoted epoxide opening/lactonization to generate the second lactone ring of alstolactine A. These results provide evidence of a biogenetic relationship between scholarisine K and alstolactine A, which should facilitate the preparation of other akuammiline-type natural products and their derivatives for functional studies. DOI: 10.1021/acs.orglett.7b00722 PMID: 28358517 4. J Am Chem Soc. 2015 May 27;137(20):6712-24. doi: 10.1021/jacs.5b03619. Epub 2015 May 14. Total Syntheses of (-)-Mersicarpine, (-)-Scholarisine G, (+)-Melodinine E, (-)-Leuconoxine, (-)-Leuconolam, (-)-Leuconodine A, (+)-Leuconodine F, and (-)-Leuconodine C: Self-Induced Diastereomeric Anisochronism (SIDA) Phenomenon for Scholarisine G and Leuconodines A and C. Xu Z(1), Wang Q(1), Zhu J(1). Author information: (1)Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH5304, CH-1015 Lausanne, Switzerland. Enantioselective total syntheses of title natural products from a common cyclohexenone derivative (S)-18 were reported. Ozonolysis of (S)-18 afforded a stable diketo ester (R)-17 that was subsequently converted to two skeletally different natural products, i.e., (-)-mersicarpine (8) with a [6.5.6.7] fused tetracyclic ring system and (-)-scholarisine G (9) with a [6.5.6.6.5] fused pentacyclic skeleton, respectively. The postcyclization diversification was realized by taking advantage of the facile conversion of (+)-melodinine E (6) to N-acyliminium ion 7, from which a hydroxy group was selectively introduced to the C6, C7, C10 and the central C21 position of diazafenestrane system, leading to (-)-leuconodine A (11), (+)-leuconodine F (12), (-)-scholarisine G (9), (-)-leuconodine C (13), and skeletally different (-)-leuconolam (5). Furthermore, an unprecedented non-natural oxabridged oxadiazafenestrane 68 was formed by oxidation of (+)-melodinine E (6). During the course of this study, a strong self-induced diastereomeric anisochronism (SIDA) phenomenon was observed for scholarisine G (9), leuconodines A (11) and C (13). X-ray structures of both the racemic and the enantiopure natural products 9, 11, and 13 were obtained. The different crystal packing of these two forms nicely explained the chemical shift differences observed in the (1)H NMR spectra of the racemic and the enantio-enriched compounds in an achiral environment. DOI: 10.1021/jacs.5b03619 PMID: 25946614 [Indexed for MEDLINE] 5. J Am Chem Soc. 2013 Dec 26;135(51):19127-30. doi: 10.1021/ja4115192. Epub 2013 Dec 13. Enantioselective total syntheses of leuconolam-leuconoxine-mersicarpine group monoterpene indole alkaloids. Xu Z(1), Wang Q, Zhu J. Author information: (1)Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne , EPFL-SB-ISIC-LSPN, BCH 5304, CH-1015 Lausanne, Switzerland. A unified strategy allowing enantioselective total syntheses of (-)-mersicarpine, (-)-scholarisine G, (+)-melodinine E, (-)-leuconoxine, and (-)-leuconolam from a common cyclohexenone derivative was reported. The Suzuki-Miyaura reaction was used to couple two simple fragments incorporating the key elements for total synthesis, and unprecedented oxidation/reduction/cyclization processes were developed that converted the substituted cyclohexenone to either a mersicarpine or leuconoxine skeleton. In a reverse biomimetic synthesis fashion, (+)-melodinine E was converted to (-)-leuconolam under acidic conditions. DOI: 10.1021/ja4115192 PMID: 24328133 [Indexed for MEDLINE]