Total Synthesis of ( ± )-α-Cubebene and ( ± )-β-Cubebene

1971 ◽  
Vol 49 (1) ◽  
pp. 12-19 ◽  
Author(s):  
Edward Piers ◽  
Ronald W. Britton ◽  
William De Waal
Keyword(s):  
Total Synthesis ◽  
Intramolecular Cyclization ◽  
High Yield ◽  
Cupric Sulfate ◽  
The Novel

An efficient total synthesis of the racemic forms of the novel tricyclic sesquiterpenes α-cubebene (1) and β-cubebene (2) is described. The key step of this synthesis involved the cupric sulfate catalyzed intramolecular cyclization of the olefinic diazoketone 3, which produced, in high yield, ( ± )-β-cubebene norketone (24) and ( ± )-1,6-epi-β-cubebene norketone (25), in a ratio of approximately 3:5, respectively.

Total synthesis of (±)-aristolone

1969 ◽  
Vol 47 (5) ◽  
pp. 831-840 ◽  
Author(s):  
Edward Piers ◽  
Ronald W. Britton ◽  
William de Waal
Keyword(s):  
Total Synthesis ◽  
Intramolecular Cyclization ◽  
Cupric Sulfate ◽  
Racemic Form

A novel and efficient total synthesis of the racemic form of the sesquiterpene (−)-aristolone (1) is presented. The key step involves the cupric sulfate catalyzed intramolecular cyclization of the diazoketone 27, which produces a mixture of products, the major component of which is (±)-aristolone.

Synthesis of benzofuranoid systems. IV. Total synthesis of cyperaquinone and conicaquinone

1978 ◽  
Vol 31 (7) ◽  
pp. 1533 ◽  
Author(s):  
JK Macleod ◽  
BR Worth ◽  
RJ Wells
Keyword(s):  
Total Synthesis ◽  
Natural Compounds ◽  
High Yield ◽  
The Novel ◽  
Site Specific ◽  
Naturally Occurring ◽  
Internal Site

The total synthesis of the novel naturally occurring benzodifuroquinones, cyperaquinone (1) and conicaquinone (2), starting from phloroglucinol is described. A comparison of synthetic and natural compounds confirmed the original structural assignments. The key intermediate in the synthesis was the 3-methylbenzofuran (21) which was prepared in high yield by an internal site-specific base-catalysed Ar1-5 cyclization of the acetonyloxy derivative (19). The method has also been applied to the syntheses of linear furocoumarins and dibenzofurans.

Conjugate systems in the construction of heterocycles and quaternary stereocenters

2007 ◽  
Vol 79 (2) ◽  
pp. 181-191 ◽  
Author(s):  
Carlos González-Romero ◽  
Pablo Bernal ◽  
Fabiola Jiménez ◽  
María del Carmen Cruz ◽  
Aydeé Fuentes-Benites ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Intramolecular Cyclization ◽  
Regioselective Synthesis ◽  
The Novel ◽  
One Pot ◽  
Naturally Occurring ◽  
Novel Approach ◽  
Michael Acceptors ◽  
Quaternary Stereocenters ◽  
Synthetic Application

The synthetic application of 4,5-bis-alkylidene-1,3-oxazolidin-2-ones led to the efficient and regioselective synthesis of 2-(3H)-benzoxazolones and diarylamines with a short methodology. They were also valuable synthons in a total synthesis of naturally occurring carbazoles. New enantiopure 4-oxazoline-2-one and 4-methylene-2-oxazolidinone were prepared via a one-pot microwave (MW)-promoted condensation of α-ketols and an enantiopure isocyanate. These enamides were efficient nucleophiles when added to Michael acceptors to give a series of compounds with quaternary stereocenters in fairly good stereoisomeric ratios. The novel approach for the synthesis of benzofurans and indoles by intramolecular cyclization of enaminones has been applied in the preparation of furobenzofurans starting from benzo-bis-enaminones.

Total Synthesis of Axially-Chiral Cannabinols: A New Platform for Cannabinoid-Based Drug Discovery

2019 ◽  
Author(s):  
Primali Navaratne ◽  
Jenny Wilkerson ◽  
Kavindri Ranasinghe ◽  
Evgeniya Semenova ◽  
Lance McMahon ◽  
...  
Keyword(s):  
Drug Discovery ◽  
Total Synthesis ◽  
Ground State ◽  
Chemical Space ◽  
Modern Medicine ◽  
The Novel ◽  
Pharmaceutical Development ◽  
Bioactive Component ◽  
Axially Chiral ◽  
New Directions

<div> <div> <div> <p>Phytocannabinoids, molecules isolated from cannabis, are gaining attention as promising leads in modern medicine, including pain management. Considering the urgent need for combating the opioid crisis, new directions for the design of cannabinoid-inspired analgesics are of immediate interest. In this regard, we have hypothesized that axially-chiral-cannabinols (ax-CBNs), unnatural (and unknown) isomers of cannabinol (CBN) may be valuable scaffolds for cannabinoid-inspired drug discovery. There are multiple reasons for thinking this: (a) ax-CBNs would have ground-state three-dimensionality akin to THC, a key bioactive component of cannabis, (b) ax-CBNs at their core structure are biaryl molecules, generally attractive platforms for pharmaceutical development due to their ease of functionalization and stability, and (c) atropisomerism with respect to phytocannabinoids is unexplored “chemical space.” Herein we report a scalable total synthesis of ax-CBNs, examine physical properties experimentally and computationally, and provide preliminary behavioral and analgesic analysis of the novel scaffolds. </p> </div> </div> </div>

Ten-Vertex Polyhedral Monocarbaborane Chemistry. The Novel High-Yield Formation of the Ten-Vertex closo Compound [6-(PMe2Ph)-closo-1-CB9H9] from the Thermolysis of [8,8-(PMe2Ph)2-nido-8,7-PtCB9H11]

1993 ◽  
Vol 58 (12) ◽  
pp. 2924-2935 ◽  
Author(s):  
Jane H. Jones ◽  
Bohumil Štíbr ◽  
John D. Kennedy ◽  
Mark Thornton-Pett
Keyword(s):  
Nmr Spectroscopy ◽  
Diffraction Analysis ◽  
High Yield ◽  
Monoclinic Space Group ◽  
The Novel ◽  
X Ray Diffraction ◽  
Metal Centre ◽  
X Ray ◽  
Yield Formation ◽  
Boiling Toluene

Thermolysis of [8,8-(PMe2Ph)2-nido-8,7-PtCB9H11] in boiling toluene solution results in an elimination of the platinum centre and cluster closure to give the ten-vertex closo species [6-(PMe2Ph)-closo-1-CB9H9] in 85% yield as a colourles air stable solid. The product is characterized by NMR spectroscopy and single-crystal X-ray diffraction analysis. Crystals (from hexane-dichloromethane) are monoclinic, space group P21/c, with a = 903.20(9), b = 1 481.86(11), c = 2 320.0(2) pm, β = 97.860(7)° and Z = 8, and the structure has been refined to R(Rw) = 0.045(0.051) for 3 281 observed reflections with Fo > 2.0σ(Fo). The clean high-yield elimination of a metal centre from a polyhedral metallaborane or metallaheteroborane species is very rare.

scholarly journals Synthesis of macrocyclic terpenoids by intramolecular cyclization. XI. Total synthesis of zerumbone.

1987 ◽  
Vol 35 (10) ◽  
pp. 4039-4042 ◽  
Author(s):  
MITSUAKI KODAMA ◽  
YOSHINORI SHIOBARA ◽  
HISAKO SUMITOMO ◽  
KAZUKO MITANI ◽  
KUMIKO UENO
Keyword(s):  
Total Synthesis ◽  
Intramolecular Cyclization

“All water chemistry” for a concise total synthesis of the novel class anti-anginal drug (RS), (R), and (S)-ranolazine

2013 ◽  
Vol 15 (3) ◽  
pp. 756 ◽  
Author(s):  
Damodara N. Kommi ◽  
Dinesh Kumar ◽  
Asit K. Chakraborti
Keyword(s):  
Total Synthesis ◽  
Water Chemistry ◽  
The Novel

ChemInform Abstract: Total Synthesis of the Novel Benzophenone NP-011694.

ChemInform ◽  
2015 ◽  
Vol 46 (48) ◽  
pp. no-no
Author(s):  
Alain Noncovich ◽  
Jane Ung ◽  
Andrew Patron
Keyword(s):  
Total Synthesis ◽  
The Novel

Total Synthesis of the Novel Spider Toxin NPTX-594 fromNephila madagascariencis

2001 ◽  
Vol 74 (9) ◽  
pp. 1743-1749 ◽  
Author(s):  
Tateaki Wakamiya ◽  
Akinori Yamamoto ◽  
Keita Kawaguchi ◽  
Tomohiko Kinoshita ◽  
Yoshihiro Yamaguchi ◽  
...  
Keyword(s):  
Total Synthesis ◽  
The Novel ◽  
Spider Toxin

Microwave synthesis, photophysical properties of novel fluorescent iminocoumarins and their application in textile printing

2015 ◽  
Vol 44 (2) ◽  
pp. 87-93 ◽  
Author(s):  
G.H. Elgemeie ◽  
K.A. Ahmed ◽  
E.A. ahmed ◽  
M.H. helal ◽  
D.M. Masoud
Keyword(s):  
Blue Light ◽  
Microwave Synthesis ◽  
Photophysical Properties ◽  
Ethyl Cyanoacetate ◽  
High Yield ◽  
The Novel ◽  
Dioxane Solution ◽  
Content Type ◽  
Textile Printing ◽  
Short Time

Purpose – This paper aims to synthesise coumarine flourescent dyes from a cheap material in a very short time with a very high yield, and by using a clean green chemistry. Design/methodology/approach – Efficient microwave synthesis for some novel iminocoumarins starts from the reaction of p-phenyl-enediamine and ethyl cyanoacetate followed by cyclocondensation with salicylaldehyde derivatives. Findings – The synthesized iminocoumarine compounds were characterized by spectroscopic methods. Absorption and fluorescence spectra of the compounds were also recorded. All compounds were fluorescent in 1,4-dioxane solution, they all emitted blue light (440-460 nm). The printing properties were studied, and their applications on printing polyester and polyamide fabrics were studied by silk screen printing. Originality/value – The authors designed efficient microwavel synthesis for some novel iminocoumarine derivatives; The novel procedure features short-reaction time, moderate yields and simple workup; All compounds were fluorescent in 1,4-dioxane solution, and they all emitted blue light; The authors studied their application in printing polyester and polyamide fabrics.

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