A short synthetic route towards merosesquiterpenes with a benzoxanthene skeleton

2014 ◽  
Vol 50 (86) ◽  
pp. 13100-13102 ◽  
Author(s):  
Antonio Fernández ◽  
Esteban Alvarez ◽  
Ramón Alvarez-Manzaneda ◽  
Rachid Chahboun ◽  
Enrique Alvarez-Manzaneda
Keyword(s):  
Diels Alder ◽  
Synthetic Route ◽  
Target Compound ◽  
Synthetic Sequence

A short synthetic sequence for the preparation of merosesquiterpenes with a benzoxanthene skeleton starting from (−)-sclareol is reported. The D ring of the target compound is obtained through a Diels–Alder cycloaddition.

Chemistry of Proximal π-Bond Systems. Part III. Synthesis of Substituted Benzopolycyclic Hydrocarbons

1975 ◽  
Vol 53 (2) ◽  
pp. 256-262 ◽  
Author(s):  
D. N. Butler ◽  
R. A. Snow
Keyword(s):  
Aromatic Ring ◽  
Diels Alder ◽  
Dimethyl Acetylenedicarboxylate ◽  
Synthetic Sequence

A series of 21 bridged, vicinal, exocyclic dimethylene hydrocarbons (1–21) have been converted to the related benzopolycyclic dimethyl esters (C1–C21) by oxidation of their respective dimethyl acetylenedicarboxylate Diels–Alder adducts (B1–B21).This synthetic sequence represents an excellent, general route to aromatic ring-substituted benzopolycyclic hydrocarbons.

The chemistry of thujone. XVI. Versatile and efficient routes to safronitrile, β-cyclogeranonitrile, β-cyclocitral, damascones, and their analogues

1992 ◽  
Vol 70 (7) ◽  
pp. 2094-2114 ◽  
Author(s):  
James P. Kutney ◽  
Philip J. Gunning ◽  
Robin G. Clewley ◽  
John Somerville ◽  
Steven J. Rettig
Keyword(s):  
Starting Material ◽  
Forest Industry ◽  
Synthetic Route ◽  
Rose Oil ◽  
Efficient Route ◽  
Synthetic Sequence

Thujone, a waste by-product of the Canadian forest industry, has been utilized as a starting material to develop a versatile synthetic route to the damascones (rose oil ketones) and related analogues. The synthetic sequence provides a route to β-cyclocitral (45), the latter having been previously converted to β-damascone (2). In addition, thujone-derived intermediates are converted to β-damascenone (48) and to intermediates that can be utilized for the preparation of damascone analogues. In conjunction with the above, an efficient route to safronitrile (42), β-cyclogeranonitrile (43), and β-cyclocitral (45) from 2,6-dimethylcyclohexanone has been developed. In summary, these studies afford an attractive versatile route to these important perfumery materials.

scholarly journals Synthesis of Novel N-Heterocyclic Compounds Containing 1,2,3-Triazole Ring System via Domino, “Click” and RDA Reactions

Molecules ◽  
2019 ◽  
Vol 24 (4) ◽  
pp. 772 ◽  
Author(s):  
Márta Palkó ◽  
Mohamed El Haimer ◽  
Zsanett Kormányos ◽  
Ferenc Fülöp
Keyword(s):  
Heterocyclic Compounds ◽  
Click Reaction ◽  
Triazole Ring ◽  
Heterocyclic Ring ◽  
Ring System ◽  
Diels Alder ◽  
Ring Closure ◽  
Synthetic Route ◽  
13C Nuclear Magnetic Resonance ◽  
Nmr Methods

An uncomplicated, high-yielding synthetic route has been developed to constitute complicated heterocycles, applying domino, click and retro-Diels–Alder (RDA) reaction sequences. Starting from 2-aminocarboxamides, a new set of isoindolo[2,1-a]quinazolinones was synthesized with domino ring closure. A click reaction was performed to create the 1,2,3-triazole heterocyclic ring, followed by an RDA reaction resulting in dihydropyrimido[2,1-a]isoindole-2,6-diones. The absolute configuration, concluded by the norbornene structure that served as a chiral source, remained constant throughout the transformations. The structure of the synthesized compounds was examined by 1H and 13C Nuclear Magnetic Resonance (NMR) methods.

scholarly journals A new synthetic route to methyl (-)-shikimate by asymmetric diels-alder reaction of (S)s-3-(2-pyridylsulfinyl)acrylate.

1988 ◽  
Vol 36 (8) ◽  
pp. 3213-3215 ◽  
Author(s):  
Tamiko Takahashi ◽  
Toshie Namiki ◽  
Yoshio Takeuchi ◽  
Toru Koizumi
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Synthetic Route ◽  
Diels Alder Reaction

scholarly journals An improved process for the preparation of pimavanserin tartrate

2019 ◽  
Vol 43 (11-12) ◽  
pp. 480-485
Author(s):  
Caijiao Wu ◽  
Qifan Zhou ◽  
Dake Song ◽  
Hui Li ◽  
Changshun Bao ◽  
...  
Keyword(s):  
Total Yield ◽  
Synthetic Route ◽  
Target Compound ◽  
Reaction Conditions

A practical synthetic route to pimavanserin tartrate, in which the target compound was obtained with 99.84% purity and in 46% total yield via a 5-step synthesis starting from 4-hydroxybenzaldehyde and (4-fluorophenyl)methanamine, is reported. The main advantages of the route include inexpensive starting materials, mild reaction conditions and an acceptable overall yield.

scholarly journals A stereoselective and flexible synthesis to access both enantiomers of N-acetylgalactosamine and peracetylated N-acetylidosamine

2018 ◽  
Vol 14 ◽  
pp. 856-860 ◽  
Author(s):  
Bettina Riedl ◽  
Walther Schmid
Keyword(s):  
Cell Signaling ◽  
Nucleophilic Substitution ◽  
Tartaric Acid ◽  
Cell Interaction ◽  
Synthetic Route ◽  
Target Compound ◽  
Stereogenic Centers ◽  
Epoxide Opening ◽  
Epoxy Alcohols ◽  
Synthetic Approaches

Synthetic approaches towards N-acetylgalactosamine (GalNAc) have been attracting considerable interest since this compound is known for its pivotal role in cell–cell interaction and receptor induced cell signaling. Herein, we present a synthetic route in which two of the four stereogenic centers present in the target compound are derived from enantiopure tartaric acid being selectively converted to epoxy alcohols. The key step is the Pd-catalyzed, stereo- and regioselective epoxide opening and subsequent nucleophilic substitution of an azide functionality. This approach enables the synthesis of the naturally D- and unnaturally L-configured GalNAc, as well as both enantiomers of the largely unknown N-acetylidosamine (IdoNAc).

scholarly journals An Improved Synthetic Route to the Potent Angiogenesis Inhibitor Benzyl Manα(1→3)-Manα(1→3)-Manα(1→3)-Manα(1→2)-Man Hexadecasulfate

2009 ◽  
Vol 62 (6) ◽  
pp. 546 ◽  
Author(s):  
Ligong Liu ◽  
Ken D. Johnstone ◽  
Jon K. Fairweather ◽  
Keith Dredge ◽  
Vito Ferro
Keyword(s):  
Building Block ◽  
Angiogenesis Inhibitor ◽  
Building Blocks ◽  
Synthetic Route ◽  
Target Compound ◽  
Angiogenic Activity

An improved synthetic route to α(1→3)/α(1→2)-linked mannooligosaccharides has been developed and applied to a more efficient preparation of the potent anti-angiogenic sulfated pentasaccharide, benzyl Manα(1→3)-Manα(1→3)-Manα(1→3)-Manα(1→2)-Man hexadecasulfate, using only two monosaccharide building blocks. Of particular note are improvements in the preparation of both building blocks and a simpler, final deprotection strategy. The route also provides common intermediates for the introduction of aglycones other than benzyl, either at the building block stage or after oligosaccharide assembly. The anti-angiogenic activity of the synthesized target compound was confirmed via the rat aortic assay.

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