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. Alkaloids Chem Biol. 2016;76:171-257. doi: 10.1016/bs.alkal.2015.08.001. Epub 2015 Sep 26. The Chemistry of the Akuammiline Alkaloids. Adams GL(1), Smith AB 3rd(2). Author information: (1)Merck Research Laboratories, West Point, PA, USA. (2)Department of Chemistry, Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, PA, USA; Monell Chemical Senses Center, Philadelphia, PA, USA. An update on the literature covering the akuammiline family of alkaloids is presented. This chapter begins with a summary of new akuammiline alkaloids reported since 2000 and is followed by an overview of new reported bioactivities of akuammiline alkaloids since 2000. The remainder of the chapter comprises a comprehensive review of the synthetic chemistry that has been reported in the last 50 years concerning akuammiline alkaloids and their structural motifs. Copyright © 2016 Elsevier Inc. All rights reserved. DOI: 10.1016/bs.alkal.2015.08.001 PMID: 26827884 [Indexed for MEDLINE] 2. 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] 3. J Am Chem Soc. 2013 Sep 4;135(35):12964-7. doi: 10.1021/ja406546k. Epub 2013 Aug 21. A concise total synthesis of (+)-scholarisine A empowered by a unique C-H arylation. Smith MW(1), Snyder SA. Author information: (1)Department of Chemistry, Columbia University, Havemeyer Hall, 3000 Broadway, New York, New York 10027, United States. The structurally unique akuammiline alkaloid (+)-scholarisine A was synthesized in 14 steps from a known enone (15 steps from commercial materials) through a route empowered by a unique C-H arylation reaction to forge its polycyclic core. Additional key steps include a pyrone Diels-Alder reaction and a radical cyclization/Keck allylation to fashion the core cage polycycle and one of the molecule's quaternary centers, as well as the use of a carefully positioned pendant hydroxyl group to facilitate the chemoselective reduction of an extremely unreactive lactam in the presence of a readily reduced lactone. DOI: 10.1021/ja406546k PMID: 23964983 [Indexed for MEDLINE] 4. J Am Chem Soc. 2013 Jan 9;135(1):519-28. doi: 10.1021/ja3111626. Epub 2012 Dec 26. Access to the akuammiline family of alkaloids: total synthesis of (+)-scholarisine A. Adams GL(1), Carroll PJ, Smith AB 3rd. Author information: (1)Department of Chemistry, Laboratory for Research on the Structure of Matter, and Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, Pennsylvania 19104, United States. The planning and implementation of an enantioselective total synthesis of (+)-scholarisine A is presented. Key tactics employed include a novel cyclization, consisting of a nitrile reduction coupled with concomitant addition of the resultant amine to an epoxide; a modified Fischer indolization; an oxidative lactonization of a diol in the presence of an indole ring; and a late-stage cyclization to complete the caged ring scaffold. The development of a possible "retro-biosynthetic" approach to other members of the akuammiline alkaloid family is also described. DOI: 10.1021/ja3111626 PMCID: PMC3557466 PMID: 23268611 [Indexed for MEDLINE] 5. J Am Chem Soc. 2012 Mar 7;134(9):4037-40. doi: 10.1021/ja211840k. Epub 2012 Jan 25. Total synthesis of (+)-scholarisine A. Adams GL(1), Carroll PJ, Smith AB 3rd. Author information: (1)Department of Chemistry, Laboratory for Research on the Structure of Matter, and Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. An effective total synthesis and assignment of the absolute configuration of the architecturally challenging compound (+)-scholarisine A has been achieved via a 20-step sequence. Highlights include a reductive cyclization involving a nitrile and an epoxide, a modified Fischer indole protocol, a late-stage oxidative lactonization, and an intramolecular cyclization leading to the indolenine ring system of (+)-scholarisine A. © 2012 American Chemical Society DOI: 10.1021/ja211840k PMCID: PMC3296875 PMID: 22280070 [Indexed for MEDLINE]