Research published in The Journal of Organic Chemistry

Synthetic Pathway of Nonpsychoactive Cannabidiol from Psychoactive Tetrahydrocannabinol: A DFT Guide.

The Journal of Organic Chemistry July 24, 2026 Sirilak Kongkaew, Waraporn Parasuk, Vudhichai Parasuk

In this study, a reaction pathway for converting the psychoactive compound Δ9-THC into the nonpsychoactive cannabidiol (CBD) was proposed. Related cannabinoids, including Δ8-THC and cannabinol (CBN), were also examined. The transformation proceeds via two key steps: (i) hydrogen elimination and cyclic ether ring cleavage, and (ii) hydrolysis to form hydroxyl groups, facilitated by boron...

DOI: 10.1021/acs.joc.6c00898 Full text

Synthetic Strategies toward Lysergic Acid Diethylamide: Ergoline Synthesis via α-Arylation, Borrowing Hydrogen Alkylation, and C-H Insertion.

The Journal of Organic Chemistry October 6, 2023 Jeremy R Tuck, Lee E. Dunlap, David E. Olson 7 citations

Lysergic acid diethylamide (LSD), a semisynthetic ergoline alkaloid analogue and hallucinogen, is a potent psychoplastogen with promising therapeutic potential. While a variety of synthetic strategies for accessing ergoline alkaloids have emerged, the complexity of the tetracyclic ring system results in distinct challenges in preparing analogues with novel substitution patterns. Methods of...

DOI: 10.1021/acs.joc.3c01363 Full text Medicinal chemistry Psychedelics Drug synthesis Molecular biology +1

Total Synthesis of 20-Norsalvinorin A. 1. Preparation of a Key Intermediate

The Journal of Organic Chemistry February 20, 2009 Ylva E. Bergman, Roger Mulder, Patrick Perlmutter 21 citations

The key tricyclic intermediate 3a, for the total synthesis of the C(20)-nor analogue of salvinorin A, was prepared in seven steps from 3-furaldehyde. Key steps involved a highly regio- and diastereoselective Lewis acid assisted Diels-Alder reaction followed by base-promoted epimerization and a completely stereoselective conjugate reduction.

DOI: 10.1021/jo802623n

Synthesis of Tricyclic Heterocycles via a Tandem Aryl Alkylation/Heck Coupling Sequence

The Journal of Organic Chemistry December 29, 2006 Dino Alberico, Alena Rudolph, Mark Lautens 60 citations

A norbornene-mediated palladium-catalyzed sequence is described in which two alkyl-aryl bonds and one alkenyl-aryl bond are formed in one pot with use of microwave irradiation. A variety of symmetrical and unsymmetrical oxygen-, nitrogen-, silicon-, and sulfur-containing tricyclic heterocycles were synthesized from a Heck acceptor and an aryl iodide containing two tethered alkyl halides. This...

DOI: 10.1021/jo0617868 Tandem Tricyclic Aryl Alkylation +9

Autoxidation of salvinorin A under basic conditions.

The Journal of Organic Chemistry November 1, 2005 Thomas A Munro, Glenn W Goetchius, Bryan L. Roth et al.

[reaction: see text] Treatment of salvinorin A (1a) with KOH in MeOH gave the enedione 3, for which the dienone structure 7 was recently proposed. Also isolated, after methylation, were the secotriesters 4a-c. A mechanism for this unusual series of autoxidations is proposed. Surprisingly, 4a showed weak affinity at the kappa-opioid receptor. Divinatorins A-C (2a-c) showed no affinity at opioid...

DOI: 10.1021/jo051813e Full text Hydroxides Potassium compounds Methanol Diterpenes, clerodane +3

Improved Fischer Indole Reaction for the Preparation of N,N-Dimethyltryptamines: Synthesis of L-695,894, a Potent 5-HT1D Receptor Agonist

The Journal of Organic Chemistry July 1, 1994 Cheng-Yi Chen, Chris H. Senanayake, Timothy J. Bill et al. 150 citations

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTImproved Fischer Indole Reaction for the Preparation of N,N-Dimethyltryptamines: Synthesis of L-695,894, a Potent 5-HT1D Receptor AgonistCheng-yi Chen, Chris H. Senanayake, Timothy J. Bill, Robert D. Larsen, Thomas R. Verhoeven, and Paul J. ReiderCite this: J. Org. Chem. 1994, 59, 13, 3738–3741Publication Date (Print):July 1, 1994Publication History...

DOI: 10.1021/jo00092a046 Citation Icon Social media Information retrieval +2

Abbreviated Ibogaine Congeners. Synthesis and Reactions of Tropan-3-yl-2- and -3-indoles. Investigation of an Unusual Isomerization of 2-Substituted Indoles Using Computational and Spectroscopic Techniques

The Journal of Organic Chemistry April 1, 1994 David B. Repke, Dean R. Artis, Janis T. Nelson et al. 40 citations

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTAbbreviated Ibogaine Congeners. Synthesis and Reactions of Tropan-3-yl-2- and -3-indoles. Investigation of an Unusual Isomerization of 2-Substituted Indoles Using Computational and Spectroscopic TechniquesDavid B. Repke, Dean R. Artis, Janis T. Nelson, and Erik H. F. WongCite this: J. Org. Chem. 1994, 59, 8, 2164–2171Publication Date (Print):April 1,...

DOI: 10.1021/jo00087a037 Isomerization Computational chemistry Combinatorial chemistry Organic chemistry +2

Divinorin A, a psychotropic terpenoid, and divinorin B from the hallucinogenic Mexican mint, Salvia divinorum

The Journal of Organic Chemistry November 1, 1984 Leander J. Valdés, William M. Butler, George M. Hatfield et al. 174 citations

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTDivinorin A, a psychotropic terpenoid, and divinorin B from the hallucinogenic Mexican mint, Salvia divinorumLeander J. Valdes III, William M. Butler, George M. Hatfield, Ara G. Paul, and Masato KoreedaCite this: J. Org. Chem. 1984, 49, 24, 4716–4720Publication Date (Print):November 1, 1984Publication History Published online1 May 2002Published...

DOI: 10.1021/jo00198a026 Hallucinogen Traditional medicine Terpenoid Pharmacology +1

Stable carbonium ions from .beta.-arylalkyl derivatives in antimony pentafluoride-sulfur dioxide (SbP5.SO2). II. Ions related to mescaline

The Journal of Organic Chemistry May 1, 1974 James A. Manner, James Cook, Brian G. Ramsey 11 citations

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTStable carbonium ions from .beta.-arylalkyl derivatives in antimony pentafluoride-sulfur dioxide (SbP5.SO2). II. Ions related to mescalineJames A. Manner, James A. Cook Jr., and Brian G. RamseyCite this: J. Org. Chem. 1974, 39, 9, 1199–1203Publication Date (Print):May 1, 1974Publication History Published online1 May 2002Published inissue 1 May...

DOI: 10.1021/jo00923a007 Carbonium ion Sulfur dioxide Inorganic chemistry

Bridged Lactones and Bridged Carbocyclic Systems from 2-(3,4,5-Trimethoxyphenyl)-4,5-dimethyl-Δ4-cyclohexenecarboxylic Acid. Novel Mescaline Analogs1

The Journal of Organic Chemistry November 1, 1963 Thomas J. Perun, Leo Zeftel, Robert G. Nelb et al. 5 citations

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTBridged Lactones and Bridged Carbocyclic Systems from 2-(3,4,5-Trimethoxyphenyl)-4,5-dimethyl-Δ4-cyclohexenecarboxylic Acid. Novel Mescaline Analogs1Thomas J. Perun, Leo Zeftel, Robert G. Nelb, and D. Stanley TarbellCite this: J. Org. Chem. 1963, 28, 11, 2937–2943Publication Date (Print):November 1, 1963Publication History Published online1 May...

DOI: 10.1021/jo01046a001 Mescaline Bicyclic molecule Medicinal chemistry Stereochemistry

Notes: The Presence of Mescaline in Opuntia cylindrica

The Journal of Organic Chemistry December 1, 1960 William B. Turner, Jack Heyman 16 citations

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTNotes: The Presence of Mescaline in Opuntia cylindricaWilliam Turner and Jack HeymanCite this: J. Org. Chem. 1960, 25, 12, 2250–2251Publication Date (Print):December 1, 1960Publication History Published online1 April 2003Published inissue 1 December 1960https://pubs.acs.org/doi/10.1021/jo01082a623https://doi.org/10.1021/jo01082a623research-articleACS...

DOI: 10.1021/jo01082a623 Mescaline Citation Icon Social media +3

Notes- Mescaline Analogs. X. 3,4-Dimethyl-, 3,4-Dichloro- and 3,5-Dimethoxy-4-methyl-β-phenethylamines

The Journal of Organic Chemistry November 1, 1960 F. Benington, R Morin, L. M. Clark 3 citations

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTNotes- Mescaline Analogs. X. 3,4-Dimethyl-, 3,4-Dichloro- and 3,5-Dimethoxy-4-methyl-β-phenethylaminesF Benington, R Morin, and L Clark, Jr.Cite this: J. Org. Chem. 1960, 25, 11, 2066–2067Publication Date (Print):November 1, 1960Publication History Published online19 March 2003Published inissue 1 November...

DOI: 10.1021/jo01081a626 Mescaline Citation Icon Phenethylamines +4

Notes - Mescaline Analogs. IX. Tetra- and Pentamethyl-β-phenethylamines

The Journal of Organic Chemistry December 1, 1958 F. Benington, R Morin, Leland C. Clark 11 citations

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTNotes - Mescaline Analogs. IX. Tetra- and Pentamethyl-β-phenethylaminesF Benington, R Morin, and Leland ClarkCite this: J. Org. Chem. 1958, 23, 12, 2034–2035Publication Date (Print):December 1, 1958Publication History Published online11 June 2003Published inissue 1 December...

DOI: 10.1021/jo01106a632 Mescaline Phenethylamines Tetra Medicinal chemistry +1

Mescaline Analogs. VIII. Substituted 5-Methoxy-and 5,6,7-Trimethoxyindoles

The Journal of Organic Chemistry 1958 F. Benington, R. D. Morin, Leland C. Clark 17 citations

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTMescaline Analogs. VIII. Substituted 5-Methoxy-and 5,6,7-TrimethoxyindolesF. BENINGTON, R. D. MORIN, and LELAND C. CLARK Jr.Cite this: J. Org. Chem. 1958, 23, 1, 19–23Publication Date (Print):January 1, 1958Publication History Published online1 May 2002Published inissue 1 January...

DOI: 10.1021/jo01095a007 Mescaline Stereochemistry Chemical reaction mechanisms

Notes - Synthsesis of 5,6,7-Trimethoxyindole Possible Intermediary Metabolite of Mescaline

The Journal of Organic Chemistry March 1, 1957 Robert Morin, F. Benington, Liz Clark 13 citations

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTNotes - Synthsesis of 5,6,7-Trimethoxyindole Possible Intermediary Metabolite of MescalineR. Morin, F. Benington, and L. Clark, Jr.Cite this: J. Org. Chem. 1957, 22, 3, 331–332Publication Date (Print):March 1, 1957Publication History Published online14 April 2003Published inissue 1 March...

DOI: 10.1021/jo01354a608 Icon Citation Altmetrics Social media +3

Notes - Mescaline Analogs. VII. 3,4,5-Trimethyl-β-phenethylamine

The Journal of Organic Chemistry March 1, 1957 F. Benington, Robert Morin, Leland C. Clark 5 citations

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTNotes - Mescaline Analogs. VII. 3,4,5-Trimethyl-β-phenethylamineF. Benington, R. Morin, and Leland Clark, Jr.Cite this: J. Org. Chem. 1957, 22, 3, 332–333Publication Date (Print):March 1, 1957Publication History Published online14 April 2003Published inissue 1 March 1957https://doi.org/10.1021/jo01354a609RIGHTS & PERMISSIONSArticle...

DOI: 10.1021/jo01354a609 Mescaline Citation Icon Altmetrics +4

Mescaline Analogs. V. p-Dialkylamino-β-phenethylamines and 9-(β-Aminoethyl)julolidine

The Journal of Organic Chemistry December 1, 1956 F. Benington, R. D. Morin, L. C. Clark 14 citations

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTMescaline Analogs. V. p-Dialkylamino-β-phenethylamines and 9-(β-Aminoethyl)julolidineF. BENINGTON, R. D. MORIN, and L. C. CLARKCite this: J. Org. Chem. 1956, 21, 12, 1470–1472Publication Date (Print):December 1, 1956Publication History Published online1 May 2002Published inissue 1 December...

DOI: 10.1021/jo01118a038 Mescaline Phenethylamines Medicinal chemistry

Notes - Mescaline Anaologs. VI. Mescaline Homologs

The Journal of Organic Chemistry December 1, 1956 F. Benington, Robert Morin, Larry Clark 8 citations

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTNotes - Mescaline Anaologs. VI. Mescaline HomologsF. Benington, R. C. Morin, and L. C. Clark, Jr.Cite this: J. Org. Chem. 1956, 21, 12, 1545–1546Publication Date (Print):December 1, 1956Publication History Published online21 February 2003Published inissue 1 December...

DOI: 10.1021/jo01118a635 Mescaline

MESCALINE ANALOGS. IV. SUBSTITUTED 4,5,6-TRIMETHOXYINDOLES

The Journal of Organic Chemistry October 1, 1955 F. Benington, R. D. Morin, Leland C. Clark 7 citations

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTMESCALINE ANALOGS. IV. SUBSTITUTED 4,5,6-TRIMETHOXYINDOLESF. BENINGTON, R. D. MORIN, and LELAND C. CLARK JR.Cite this: J. Org. Chem. 1955, 20, 10, 1454–1457Publication Date (Print):October 1, 1955Publication History Published online1 May 2002Published inissue 1 October...

DOI: 10.1021/jo01127a026 Mescaline Stereochemistry

MESCALINE ANALOGS. III. 2,4,6-TRIALKYL- AND 3,4-DIHYDROXY-5-METHOXY-β-PHENETHYLAMINES

The Journal of Organic Chemistry September 1, 1955 F. Benington, R. D. Morin, Leland C. Clark 8 citations

ADVERTISEMENT RETURN TO ISSUEPREVArticleMESCALINE ANALOGS. III. 2,4,6-TRIALKYL- AND 3,4-DIHYDROXY-5-METHOXY-β-PHENETHYLAMINESF. BENINGTON, R. D. MORIN, and LELAND C. CLARK JR.Cite this: J. Org. Chem. 1955, 20, 9, 1292–1296Publication Date (Print):September 1, 1955Publication History Published online1 May 2002Published inissue 1 September...

DOI: 10.1021/jo01126a019 Mescaline Phenethylamines Stereochemistry Medicinal chemistry

MESCALINE ANALOGS. II. TETRA- AND PENTA-METHOXY-β-PHENETHYLAMINES

The Journal of Organic Chemistry 1955 F. Benington, R. D. Morin, Leland C. Clark 38 citations

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTMESCALINE ANALOGS. II. TETRA- AND PENTA-METHOXY-β-PHENETHYLAMINESF. BENINGTON, R. D. MORIN, and LELAND C. CLARK JR.Cite this: J. Org. Chem. 1955, 20, 1, 102–108Publication Date (Print):January 1, 1955Publication History Published online1 May 2002Published inissue 1 January...

DOI: 10.1021/jo01119a017 Mescaline Phenethylamines Tetra Medicinal chemistry

MESCALINE ANALOGS. I. 2,4,6-TRIALKOXY-β-PHENETHYLAMINES

The Journal of Organic Chemistry 1954 F. Benington, R. D. Morin, Leland C. Clark 13 citations

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTMESCALINE ANALOGS. I. 2,4,6-TRIALKOXY-β-PHENETHYLAMINESF. BENINGTON, R. D. MORIN, and LELAND C. CLARK JR.Cite this: J. Org. Chem. 1954, 19, 1, 11–16Publication Date (Print):January 1, 1954Publication History Published online1 May 2002Published inissue 1 January...

DOI: 10.1021/jo01366a003 Mescaline Phenethylamines Pharmacology Stereochemistry

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