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Academic literature on the topic 'Salvinorin A'

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Published: 4 June 2021
Last updated: 1 August 2024

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Journal articles on the topic "Salvinorin A"

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Su, Diansan, John Riley, Willis J. Kiessling, William M. Armstead, and Renyu Liu. "Salvinorin A Produces Cerebrovasodilation through Activation of Nitric Oxide Synthase, κ Receptor, and Adenosine Triphosphate–sensitive Potassium Channel." Anesthesiology 114, no. 2 (February 1, 2011): 374–79. http://dx.doi.org/10.1097/aln.0b013e318204e029.

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Background Salvinorin A is a nonopioid, selective κ opioid-receptor agonist. Despite its high potential for clinical application, its pharmacologic profile is not well known. In the current study, we hypothesized that salvinorin A dilates pial arteries via activation of nitric oxide synthase, adenosine triphosphate-sensitive potassium channels, and opioid receptors. Methods Cerebral artery diameters and cyclic guanosine monophosphate in cortical periarachnoid cerebrospinal fluid were monitored in piglets equipped with closed cranial windows. Observation took place before and after salvinorin A administration in the presence or absence of an opioid antagonist (naloxone), a κ opioid receptor-selective antagonist (norbinaltorphimine), nitric oxide synthase inhibitors (N(G)-nitro-L-arginine and 7-nitroindazole), a dopamine receptor D2 antagonist (sulpiride), and adenosine triphosphate-sensitive potassium and Ca-activated K channel antagonists (glibenclamide and iberiotoxin). The effects of salvinorin A on the constricted cerebral artery induced by hypocarbia and endothelin were investigated. Data were analyzed by repeated measures ANOVA (n = 5) with statistical significance set at a P value of less than 0.05. Results Salvinorin A induced immediate but brief vasodilatation that was sustained for 30 min via continual administration every 2 min. Vasodilatation and the associated cyclic guanosine monophosphate elevation in cerebrospinal fluid were abolished by preadministration N(G)-nitro-L-arginine, but not 7-nitroindazole. Although naloxone, norbinaltorphimine, and glibenclamide abolished salvinorin A-induced cerebrovasodilation, this response was unchanged by iberiotoxin and sulpiride. Hypocarbia and endothelin-constricted pial arteries responded similarly to salvinorin A, to the extent observed under resting tone. Conclusions Salvinorin A dilates cerebral arteries via activation of nitric oxide synthase, adenosine triphosphate-sensitive potassium channel, and the κ opioid receptor.
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Braida, Daniela, Andrea Donzelli, Roberta Martucci, Valeria Capurro, and Mariaelvina Sala. "Learning and Memory Impairment Induced by Salvinorin A, the Principal Ingredient of Salvia divinorum, in Wistar Rats." International Journal of Toxicology 30, no. 6 (September 29, 2011): 650–61. http://dx.doi.org/10.1177/1091581811418538.

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The effects of salvinorin A ( Salvia divinorum principal ingredient), a potent κ-opioid natural hallucinogen, on learning and memory were investigated. Wistar rats were tested in the 8-arm radial maze, for object recognition and passive avoidance tasks for spatial, episodic, and aversive memory. Attention was assessed using a latent inhibition task. Salvinorin A (80-640 μg/kg subcutaneous [sc]) did not affect short-term memory, but it impaired spatial long-term memory. Episodic and aversive memories were impaired by salvinorin A (160-640 μg/kg). Memory impairment was blocked by the selective κ-opioid receptor antagonist, nor-binaltorphimine ([nor-B]; 0.5-1 mg/kg, intraperitoneal [ip]). Salvinorin A (160 μg/kg) disrupted latent inhibition, after LiCl treatment, such as reduced sucrose intake, suggesting an attention would result in an impairment of cognitive behavior. These findings demonstrate for the first time that salvinorin A has deleterious effects on learning and memory, through a κ-opioid receptor mechanism.
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Brito-da-Costa, Andreia Machado, Diana Dias-da-Silva, Nelson G. M. Gomes, Ricardo Jorge Dinis-Oliveira, and Áurea Madureira-Carvalho. "Pharmacokinetics and Pharmacodynamics of Salvinorin A and Salvia divinorum: Clinical and Forensic Aspects." Pharmaceuticals 14, no. 2 (February 3, 2021): 116. http://dx.doi.org/10.3390/ph14020116.

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Salvia divinorum Epling and Játiva is a perennial mint from the Lamiaceae family, endemic to Mexico, predominantly from the state of Oaxaca. Due to its psychoactive properties, S. divinorum had been used for centuries by Mazatecans for divinatory, religious, and medicinal purposes. In recent years, its use for recreational purposes, especially among adolescents and young adults, has progressively increased. The main bioactive compound underlying the hallucinogenic effects, salvinorin A, is a non-nitrogenous diterpenoid with high affinity and selectivity for the κ-opioid receptor. The aim of this work is to comprehensively review and discuss the toxicokinetics and toxicodynamics of S. divinorum and salvinorin A, highlighting their psychological, physiological, and toxic effects. Potential therapeutic applications and forensic aspects are also covered in this review. The leaves of S. divinorum can be chewed, drunk as an infusion, smoked, or vaporised. Absorption of salvinorin A occurs through the oral mucosa or the respiratory tract, being rapidly broken down in the gastrointestinal system to its major inactive metabolite, salvinorin B, when swallowed. Salvinorin A is rapidly distributed, with accumulation in the brain, and quickly eliminated. Its pharmacokinetic parameters parallel well with the short-lived psychoactive and physiological effects. No reports on toxicity or serious adverse outcomes were found. A variety of therapeutic applications have been proposed for S. divinorum which includes the treatment of chronic pain, gastrointestinal and mood disorders, neurological diseases, and treatment of drug dependence. Notwithstanding, there is still limited knowledge regarding the pharmacology and toxicology features of S. divinorum and salvinorin A, and this is needed due to its widespread use. Additionally, the clinical acceptance of salvinorin A has been hampered, especially due to the psychotropic side effects and misuse, turning the scientific community to the development of analogues with better pharmacological profiles.
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Socała, Katarzyna, Urszula Doboszewska, and Piotr Wlaź. "Salvinorin A Does Not Affect Seizure Threshold in Mice." Molecules 25, no. 5 (March 7, 2020): 1204. http://dx.doi.org/10.3390/molecules25051204.

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The κ-opioid receptor has recently gained attention as a new molecular target in the treatment of many psychiatric and neurological disorders including epilepsy. Salvinorin A is a potent plant-derived hallucinogen that acts as a highly selective κ-opioid receptor agonist. It has unique structure and pharmacological properties, but its influence on seizure susceptibility has not been studied so far. Therefore, the aim of the present study was to investigate the effect of salvinorin A on seizure thresholds in three acute seizure tests in mice. We also examined its effect on muscular strength and motor coordination. The obtained results showed that salvinorin A (0.1–10 mg/kg, i.p.) did not significantly affect the thresholds for the first myoclonic twitch, generalized clonic seizure, or forelimb tonus in the intravenous pentylenetetrazole seizure threshold test in mice. Likewise, it failed to affect the thresholds for tonic hindlimb extension and psychomotor seizures in the maximal electroshock- and 6 Hz-induced seizure threshold tests, respectively. Moreover, no changes in motor coordination (assessed in the chimney test) or muscular strength (assessed in the grip-strength test) were observed. This is a preliminary report only, and further studies are warranted to better characterize the effects of salvinorin A on seizure and epilepsy.
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Hill, Sarah J., Aurélien U. C. M. Brion, and Ryan A. Shenvi. "Chemical syntheses of the salvinorin chemotype of KOR agonist." Natural Product Reports 37, no. 11 (2020): 1478–96. http://dx.doi.org/10.1039/d0np00028k.

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Ostrozhenkova, E. G. "Biosynthesis of salvinorin A." IOP Conference Series: Earth and Environmental Science 613 (December 23, 2020): 012101. http://dx.doi.org/10.1088/1755-1315/613/1/012101.

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Munro, Thomas A., Douglas M. Ho, and Bruce M. Cohen. "Salvinorin B methoxymethyl ether." Acta Crystallographica Section E Structure Reports Online 68, no. 11 (October 27, 2012): o3225—o3226. http://dx.doi.org/10.1107/s1600536812043449.

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Hagiwara, Hisahiro, Takashi Nojima, Yuhki Suka, Takashi Hoshi, and Toshio Suzuki. "First Total Synthesis of the Neo-Clerodane Diterpenoid Salvinorin F." Natural Product Communications 6, no. 3 (March 2011): 1934578X1100600. http://dx.doi.org/10.1177/1934578x1100600306.

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Line, Nathan J., Aaron C. Burns, Sean C. Butler, Jerry Casbohm, and Craig J. Forsyth. "Total Synthesis of (−)-Salvinorin A." Chemistry - A European Journal 22, no. 50 (November 4, 2016): 17983–86. http://dx.doi.org/10.1002/chem.201604853.

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Tsujikawa, Kenji, Kenji Kuwayama, Hajime Miyaguchi, Tatsuyuki Kanamori, Yuko T. Iwata, Takemi Yoshida, and Hiroyuki Inoue. "Determination of salvinorin A and salvinorin B in Salvia divinorum-related products circulated in Japan." Forensic Science International 180, no. 2-3 (September 2008): 105–9. http://dx.doi.org/10.1016/j.forsciint.2008.07.008.

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Dissertations / Theses on the topic "Salvinorin A"

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LaBelle, Keri Lyn. "Development of presumptive macroscopic, microscopic, and colorimetric tests for Salvia divinorum, salvinorin A, and salvinorin B." Thesis, Boston University, 2012. https://hdl.handle.net/2144/12463.

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Thesis (M.S.)--Boston University PLEASE NOTE: Boston University Libraries did not receive an Authorization To Manage form for this thesis or dissertation. It is therefore not openly accessible, though it may be available by request. If you are the author or principal advisor of this work and would like to request open access for it, please contact us at open-help@bu.edu. Thank you.
Salvia divinorum (S. divinorum) is a psychoactive plant from the Lamiaceae (mint) family originating in the Oaxaca region of Mexico. The plant's psychoactive compound, salvinorin A (sal A) has been found to be unique to the microscopic glands of S. divinorum and exhibit powerful psychoactive properties similar to lysergic acid diethylamide (LSD) at concentrations as low as 200 µg. A similar compound, salvinorin B (sal B), is also found in the glands of S. divinorum and does not have psychoactive properties, although is considered a precursor to sal A. The plant is traditionally used by the Mazatec Indians for divination and healing rituals but has since been brought to the United States (U.S.) where it has become a popular drug of abuse. The plant is abused like other psychoactive plants such as mescaline, psilocybin mushrooms, and cannabis, and is currently not regulated by federal laws. In anticipation of legislation regulating S. divinorum, sal A, and sal B, forensic analysis methods must be improved to allow for the rapid and accurate identification of plant material, such as fresh or dried leaves, and the active compounds. Currently, analysis of S. divinorum relies on the identification of sal A from extracts of leaf material, a time consuming process requiring sophisticated instrumentation. The development of preliminary tests such as a macroscopic/microscopic analysis or colorimetric spot test would allow for the rapid analysis of S. divinorum plant material, sal A, and sal B, and would allow for elimination of non- S. divinorum material from further time-consuming analyses. This research focused on examining the botanical features of S. divinorum plant material at the macroscopic and microscopic level for the ability to discriminate S. divinorum from other plants in the same taxonomic family and common household herbs. Additionally, a colorimetric test utilizing in-house preparations of the Ehrlich's reagent was evaluated for its potential to be used as a presumptive test for S. divinorum, sal A, and sal B. [TRUNCATED]
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Lingham, Anthony, and arlingham@hotmail com. "Studies Toward the Synthesis of Salvinorin A." RMIT University. Applied Sciences, 2008. http://adt.lib.rmit.edu.au/adt/public/adt-VIT20080428.095126.

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Salvinorin A [(2S,4aR,6aR,7R,9S,10aS,10bR)-9-(acetyloxy)-2-(3-furanyl)-dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naptho[2,1-c]pyran-7-carboxylic acid methyl ester] is a trans-neoclerodane diterpene from the leaves of the hallucinogenic Mexican sage Salvia divinorum and has been identified as the principal psychoactive component in this plant of traditional spiritual importance. Salvinorin A is the most potent naturally occurring hallucinogen found so far and is reported to act selectively as a ƒÛ-opioid receptor agonist. Synthetic modification of the natural product has contributed to a number of proposed pharmacophores to identify the key structural features necessary for biological activity and a direct strategy for the asymmetric synthesis of the natural product is desirable since it allows access to a more diverse range of analogues. An ambitious retrosynthetic study of salvinorin A indicated the C(3)-heterosubstituted furan as an appropriate starting material for a Diels-Alder approach towards the ketone ring of the natural product. An expedient and high yielding methodology for the preparation of 3-furylamines is described, allowing the flexible introduction of alkyl substituents in the C(5) position. Optically pure ephedrine isomers have been explored as chiral amine auxiliaries and have been successfully attached as 3-furylamine substituents using the general methodology described. The 3-furylamines are electron rich dienes that are highly reactive towards Diels-Alder cycloaddition reactions with methyl acrylate. Diastereoisomers of the 7-oxanorbornane species methyl 1-methyl-5-oxo-7-oxa-bicyclo[2.2.1]heptane-2-carboxylate were prepared as new compounds from the hydrolysis of Diels-Alder cycloadducts and are functionalised bicyclic intermediates to access the ketone of the natural product. Diels-Alder reactions between the non-racemic (2S)-ephedrine-derived furans and methyl acrylate gave spiro-oxazolidine adducts that underwent hydrolysis to give the desired ketone. X-ray crystallography data for the derivatised cycloadduct established diastereoselectivity in favor of the (1S,4S)-enantiomer, as desired for the asymmetric natural product synthesis. A procedure for the ether cleavage of methyl 1-methyl-5-oxo-7-oxa-bicyclo[2.2.1]heptane-2-carboxylate was required to access the convergent precursor methyl 5-acetoxy-2-methyl-4-oxocyclohex-2-enecarboxylate. Successful C-O cleavage was achieved using Lewis-acid catalysis with BBr3 followed by mixing with the hindered base 2,4,6-collidine to yield methyl 5-hydroxy-2-methyl-4-oxocyclohex-2-enecarboxylate albeit only at high dilution. Acetylation proceeded in excellent yield in the same reaction vessel to give methyl 1-methyl-5-oxo-7-oxa-bicyclo[2.2.1]heptane-2-carboxylate in excellent yield. The devised synthetic pathway is shown to successfully construct the ketone ring of salvinorin A and stereoselectivity for the (1S,4S)-enantiomer can be achieved using the ephedrine derived furans as desired for the asymmetric natural product synthesis. The ƒÔ-lactone ring 6-(furan-3-yl)-5,6-dihydro-4-methyl-3-vinylpyran-2-one was derived from rudimentary precursors as a convergent reagent to introduce the lactone ring of salvinorin A. A short synthesis for the racemic compound is described starting from the aldol reaction between 3-furaldehyde and acetone to give the 3-furfurol, 4-(furan-3-yl)-4-hydroxybutan-2-one in quantitative yield. The 3-furfurol was reacted to form the ƒÑ-bromovinyl ester, 1-(furan-3-yl)-3-oxobutyl 2-bromobut-3-enoate using a deconjugation/esterification protocol with 2-bromobut-3-enoyl chloride. Intramolecular ring closure to the ƒÔ-lactone was achieved using a Reformatsky reaction and dehydration under acidic conditions yielded the racemic convergent precursor 6-(furan-3-yl)-5,6-dihydro-4-methyl-3-vinylpyran-2-one in high yield. A possible strategy for joining the ketone and lactone fragments for the total synthesis of salvinorin A is proposed.
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McGovern, Donna. "Salvinorin A: Fragment Synthesis and Modeling Studies." VCU Scholars Compass, 2009. http://scholarscompass.vcu.edu/etd/1862.

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Salvinorin A is a non-nitrogenous, selective kappa opioid receptor agonist with potent hallucinogenic properties. Because Salvinorin A has no basic nitrogen, it does not readily adhere to the “message-address” concept of selectivity for the opioid receptors. Therefore, a better understanding of how salvinorin A and its analogs interact with the kappa opioid receptor may shed some light on how salvinorin A obtains its potency and selectivity. The structure-affinity relationships (SAFIR) of salvinorin A and its analogs along with a discussion of the selectivity of the opioid receptors, is presented. A fragment of salvinorin A, methyl-3-acetoxy-4-oxocyclohexanecarboxylate, was synthesized to determine if the B, C and D rings are or are not necessary for binding to the opioid receptors. The fragment was found not to bind to the kappa, delta or mu receptor which reinforces the importance of the B, C and D rings in the binding of salvinorin A to the kappa opioid receptor. Homology models of the kappa, delta and mu opioid receptors were constructed based on inactive bovine rhodopsin, light-activated bovine rhodopsin and the human beta-2 adrenergic receptors. The program MODELLER was also used to construct the kappa opioid receptor. Two comparative molecular field analysis (CoMFA) studies are then presented which compared three different types of alignment methods. The alignment methods employed included a receptor-docked alignment in which the salvinorin A analogs were docked into a model of the kappa opioid receptor using the program GOLD. The docked poses for this alignment were chosen based on their similarity to our postulated model of salvinorin A in the kappa opioid receptor. In our model the furan oxygen forms hydrogen bonds with Q115(2.60) and Y320(7.43), the methoxy oxygen of the C-4 position ester group may form a hydrogen bond with Y312(7.35) and the methyl group of the C-2 position acetoxy moiety forms a hydrophobic interaction with Y313(7.36). These interactions are consistent with mutagenesis studies. The other alignment methods employed were a FlexS alignment and a realignment of the receptor-docked poses using the Fit Atoms function within SYBYL. Only the receptor-docked alignment method resulted in robust and predictive CoMFA models which indicates that the analogs may bind to the kappa opioid receptor in a similar but non-identical way. In addition, information from the CoMFA models based on the receptor-docked alignment led to a postulated binding mode for a set of amine analogs of salvinorin A which were not part of the original data set. Docking studies have the positively charged C-2 position amine group interacting with E209(XL2.49) while the furan oxygen and C-4 position ester group interacts with the same residues as in our model of salvinorin A in the kappa opioid receptor. The studies presented here not only support our postulated model of salvinorin A binding to the kappa opioid receptor but may also explain the trend of the beta epimers of the amine analogs to have a higher affinity than the corresponding alpha epimers. Site-directed mutagenesis studies could provide data to support or refute the postulated models of the amines docked in the kappa opioid receptor presented here.
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Butler, Sean Colin. "Construction of the Carbon Skeleton of Salvinorin A." The Ohio State University, 2011. http://rave.ohiolink.edu/etdc/view?acc_num=osu1306524854.

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Casbohm, Jerry S. "Modifications to the Synthesis of the Salvinorin A Carbon Skeleton." The Ohio State University, 2016. http://rave.ohiolink.edu/etdc/view?acc_num=osu1462816273.

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Line, Nathan. "Total Synthesis of Salvinorin A via an IMDA-Tsuji Allylation Strategy." The Ohio State University, 2016. http://rave.ohiolink.edu/etdc/view?acc_num=osu1461161309.

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Yan, Feng. "Molecular mechanisms by which salvinorin A binds to and activates the k-opioid receptor." Cleveland, Ohio : Case Western Reserve University, 2008. http://rave.ohiolink.edu/etdc/view?acc%5Fnum=case1207342013.

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Kutrzeba, Lukasz. "Biosynthesis of Salvinorin A, : a potent hallucinogen from Salvia Divinorum Epling & Jativa /." Full text available from ProQuest UM Digital Dissertations, 2009. http://0-proquest.umi.com.umiss.lib.olemiss.edu/pqdweb?index=0&did=1804960241&SrchMode=1&sid=12&Fmt=2&VInst=PROD&VType=PQD&RQT=309&VName=PQD&TS=1269370294&clientId=22256.

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Yan, Feng. "Molecular Mechanisms by which Salvinorin A Binds to and Activates the κ-Opioid Receptor." Case Western Reserve University School of Graduate Studies / OhioLINK, 2008. http://rave.ohiolink.edu/etdc/view?acc_num=case1207342013.

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McGee, Philippe. "Application of Gold(I) Catalysis in the Synthesis of Bridged Carbocycles, (±)-Magellanine and (±)-Salvinorin A." Thesis, Université d'Ottawa / University of Ottawa, 2018. http://hdl.handle.net/10393/38485.

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Gold was considered for a long time to be an inert metal and was only in 1986 that the first homogeneous gold-catalyzed transformation was reported. In our laboratory, we isolated a surprisingly stable vinyl complex that resulted from an unexpected 1,2-silyl migration while working on a gold(I)-catalyzed reaction for the synthesis of polyprenylated polycyclic acylphloroglucinols (PPAPs). We herein report the isolation of a variety of organogold species where we could control the silyl migration based on the nature of the silyl group installed on the terminal alkyne. Silyl groups bearing an aromatic ring inhibited the silyl migration while the aliphatic silyl group afforded the 1,2-silyl migrated adduct. After mechanistic investigation of this intriguing migration, we believe that this process goes through a relatively rare gold vinylidene intermediate. More than 15 organogold complexes were isolated in good yield and characterized by x-ray crystallography. Investigation of their reactivity led to the formation of C(sp3)-C(sp2) bonds using electrophilic reagents without the use of Pd-based catalysts. We have also developed a new gold(I)-catalyzed dehydro Diels-Alder reaction using a simple monocyclic silyl enol ether. This methodology proceeds effectively with a wide scope by the use of [JackiephosAu(NCMe)]SbF6 in toluene. This methodology was then applied to the synthesis of magellanine, an architecturally complexed angular natural product isolated in 1976 from the club moss Lycopodium Magellanicum. The key step precursor was rapidly constructed via a Mitsunobu/Diels-Alder reaction that generated the requisite carboxaldehyde. The dehydro Diels-Alder reaction afforded the molecular skeleton of magellanine diastereoselectively in 91% yield. The synthesis was successfully accomplished in 11 steps demonstrating the ability of the gold(I) salt to rapidly construct complex molecules. Since the discovery of salvinorin A, a lot of efforts were exerted in order to optimize the biological activity for treatment of central nervous system disorders. Development of a new synthetic routes to salvinorins are essential to afford novel functionalized analogues. The decalin framework of salvinorin A was assembled with a Diels-Alder reaction with Et2AlCl followed by a gold(I)-catalyzed 6-endo-dig carbocyclization with [JohnphosAu(NCMe)]SbF6. Further functionalization afforded an elaborated intermediate which possesses the correct stereochemistry of the natural product. Following these promising results, efforts are currently in progress for the completion of the total synthesis.
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Books on the topic "Salvinorin A"

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Turner, D. M. Salvinorin: The psychedelic essence of Salvia divinorum. San Francisco, CA: Panther Press, 1996.

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Lawrence, Jonathan Farrel. I. Studies toward the total synthesis of eleutherobin: II. Total synthesis of salvinorin A. 2008.

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Book chapters on the topic "Salvinorin A"

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"Salvia divinorumEpling & Jativa and Salvinorin A." In Medical Toxicology of Drug Abuse, 961–67. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2012. http://dx.doi.org/10.1002/9781118105955.ch65.

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Tanaka, Hiroyuki, Madan Kumar Paudel, Osamu Shirota, Kaori Sasaki-Tabata, Setsuko Sekita, and Satoshi Morimoto. "Enzyme Immunoassay for Salvinorin A (a Main Component in Salvia divinorum )." In Neuropathology of Drug Addictions and Substance Misuse, 749–56. Elsevier, 2016. http://dx.doi.org/10.1016/b978-0-12-800212-4.00070-4.

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Butelman, Eduardo R., and Mary Jeanne Kreek. "The Widely Available Hallucinogenic Plant Salvia divinorum and Its Main Component, Salvinorin A." In Neuropathology of Drug Addictions and Substance Misuse, 739–46. Elsevier, 2016. http://dx.doi.org/10.1016/b978-0-12-800212-4.00069-8.

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"Salvinorin A: Example of a Non-Alkaloidal Bioactive Opioid from a Plant Source." In Kratom and Other Mitragynines, 56–73. CRC Press, 2014. http://dx.doi.org/10.1201/b17666-8.

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"8-Epi-Salvinorin B: Crystal Structure and Affinity at the K Opioid Receptor." In Organic Chemistry, 264–70. Apple Academic Press, 2011. http://dx.doi.org/10.1201/b12874-28.

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Kivell, Bronwyn M., Amy W. M. Ewald, and Thomas E. Prisinzano. "Salvinorin A Analogs and Other Kappa-Opioid Receptor Compounds as Treatments for Cocaine Abuse." In Emerging Targets & Therapeutics in the Treatment of Psychostimulant Abuse, 481–511. Elsevier, 2014. http://dx.doi.org/10.1016/b978-0-12-420118-7.00012-3.

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