On the synthesis of cardioactive steroid glycosides. On cardioactive steroids. XI

1983 ◽  
Vol 61 (10) ◽  
pp. 2442-2444 ◽  
Author(s):  
Haolun Jin ◽  
Thomas Y. R. Tsai ◽  
Karbl Wiesner
Keyword(s):  
Total Synthesis ◽  
Fundamental Importance ◽  
High Yield ◽  
Urethane Group ◽  
Steroid Glycosides ◽  
Cardioactive Steroids ◽  
First Time

A stereoselective β-glycosidation of digitoxose and digitoxigenin involving a 1–3 participation of a urethane group is described. The conversion of digitoxin (10) to its furyl derivative 11 and the rcoxidation of 11 to digitoxin and isodigitoxin (12), respectively, in high yield is reported for the first time. This is of fundamental importance for the use of the new glycosidation method in the total synthesis of digitoxin and its analogues.

scholarly journals First total synthesis of kipukasin A

2017 ◽  
Vol 13 ◽  
pp. 855-862 ◽  
Author(s):  
Chuang Li ◽  
Haixin Ding ◽  
Zhizhong Ruan ◽  
Yirong Zhou ◽  
Qiang Xiao
Keyword(s):  
Total Synthesis ◽  
Starting Material ◽  
Practical Approach ◽  
High Yield ◽  
Protecting Group ◽  
First Time

In this paper, a practical approach for the total synthesis of kipukasin A is presented with 22% overall yield by using tetra-O-acetyl-β-D-ribose as starting material. An improved iodine-promoted acetonide-forming reaction was developed to access 1,2-O-isopropylidene-α-D-ribofuranose. For the first time, ortho-alkynylbenzoate was used as protecting group for the 5-hydoxy group. After subsequent Vorbrüggen glycosylation, the protecting group could be removed smoothly in the presence of 5 mol % Ph3PAuOTf in dichloromethane to provide kipukasin A in high yield and regioselectivity.

The Smoulder Stream of Cigarettes / Zur Kenntnis des Glimmstromes von Cigaretten

1965 ◽  
Vol 3 (2) ◽  
Author(s):  
F. Seehofer ◽  
W. Schulz
Keyword(s):  
Moisture Content ◽  
Spatial Position ◽  
High Yield ◽  
Physical Conditions ◽  
Moisture Contents ◽  
Cigarette Paper ◽  
First Time

AbstractThe phenomenon of the smoulder stream flowing through the cigarette during smouldering and during the puff intervals is demonstrated for the first time and its dependence upon physical conditions is examined. The volume of the smoulder stream can amount up to 180 ml per cigarette. Increasing draw resistance of the cigarette and augmenting moisture content of the tobacco as well as perforation of the cigarette paper have a decreasing effect on volume and velocity of the smoulder stream. The porosity of the cigarette paper has no perceptible influence. The spatial position of the cigarette affects volume and velocity of the smoulder stream. The influence exercised by the smoulder stream on the yields of total condensate, nicotine, phenols, aldehydes, and acroleine when the cigarette tip is open during the puff intervals is determined. When the moisture contents of the tobacco were extremely high, yield decreases reaching 50 % could be observed.

Iridium-Catalyzed Silylation of C-H bonds in Unactivated Arenes: A Sterically-Encumbered Phenanthroline Ligand Accelerates Catalysis Enabling New Reactivity

2019 ◽  
Author(s):  
Caleb Karmel ◽  
Zhewei Chen ◽  
John Hartwig
Keyword(s):  
High Activity ◽  
Functional Group ◽  
Activity Analysis ◽  
High Reactivity ◽  
High Yield ◽  
Phen Ligand ◽  
Mechanistic Studies ◽  
Phenanthroline Ligand ◽  
First Time ◽  
New System

We report a new system for the silylation of aryl C-H bonds. The combination of [Ir(cod)(OMe)]<sub>2</sub> and 2,9-Me<sub>2</sub>-phenanthroline (2,9-Me<sub>2</sub>phen) catalyzes the silylation of arenes at lower temperatures and with faster rates than those reported previously, when the hydrogen byproduct is removed, and with high functional group tolerance and regioselectivity. Inhibition of reactions by the H<sub>2</sub> byproduct is shown to limit the silylation of aryl C-H bonds in the presence of the most active catalysts, thereby masking their high activity. Analysis of initial rates uncovered the high reactivity of the catalyst containing the sterically hindered 2,9-Me<sub>2</sub>phen ligand but accompanying rapid inhibition by hydrogen. With this catalyst, under a flow of nitrogen to remove hydrogen, electron-rich arenes, including those containing sensitive functional groups, undergo silylation in high yield for the first time, and arenes that underwent silylation with prior catalysts react over much shorter times with lower catalyst loadings. The synthetic value of this methodology is demonstrated by the preparation of key intermediates in the synthesis of medicinally important compounds in concise sequences comprising silylation and functionalization. Mechanistic studies demonstrate that the cleavage of the aryl C-H bond is reversible and that the higher rates observed with the 2,9-Me<sub>2</sub>phen ligand is due to a more thermodynamically favorable oxidative addition of aryl C-H bonds.

The Total Synthesis of Rhabdastrellic Acid A

2018 ◽  
Author(s):  
Yaroslav Boyko ◽  
Christopher Huck ◽  
David Sarlah
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Cross Coupling ◽  
Side Chains ◽  
General Strategy ◽  
Modular Approach ◽  
Linear Sequence ◽  
Generating Sequence ◽  
First Time

<div>The first total synthesis of rhabdastrellic acid A, a highly cytotoxic isomalabaricane triterpenoid, has been accomplished in a linear sequence of 14 steps from commercial geranylacetone. The prominently strained <i>trans-syn-trans</i>-perhydrobenz[<i>e</i>]indene core characteristic of the isomalabaricanes is efficiently accessed in a selective manner for the first time through a rapid, complexity-generating sequence incorporating a reductive radical polyene cyclization, an unprecedented oxidative Rautenstrauch cycloisomerization, and umpolung 𝛼-substitution of a <i>p</i>-toluenesulfonylhydrazone with in situ reductive transposition. A late-stage cross-coupling in concert with a modular approach to polyunsaturated side chains renders this a general strategy for the synthesis of numerous family members of these synthetically challenging and hitherto inaccessible marine triterpenoids.</div>

scholarly journals Bacterial cellulose spheroids as building blocks for 3D and patterned living materials and for regeneration

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Joaquin Caro-Astorga ◽  
Kenneth T. Walker ◽  
Natalia Herrera ◽  
Koon-Yang Lee ◽  
Tom Ellis
Keyword(s):  
Bacterial Cellulose ◽  
Building Blocks ◽  
Genetically Engineered ◽  
High Yield ◽  
Synthetic Materials ◽  
Chemical Inputs ◽  
First Time ◽  
3D Shapes ◽  
Promising Avenue ◽  
Living Materials

AbstractEngineered living materials (ELMs) based on bacterial cellulose (BC) offer a promising avenue for cheap-to-produce materials that can be programmed with genetically encoded functionalities. Here we explore how ELMs can be fabricated in a modular fashion from millimetre-scale biofilm spheroids grown from shaking cultures of Komagataeibacter rhaeticus. Here we define a reproducible protocol to produce BC spheroids with the high yield bacterial cellulose producer K. rhaeticus and demonstrate for the first time their potential for their use as building blocks to grow ELMs in 3D shapes. Using genetically engineered K. rhaeticus, we produce functionalized BC spheroids and use these to make and grow patterned BC-based ELMs that signal within a material and can sense and report on chemical inputs. We also investigate the use of BC spheroids as a method to regenerate damaged BC materials and as a way to fuse together smaller material sections of cellulose and synthetic materials into a larger piece. This work improves our understanding of BC spheroid formation and showcases their great potential for fabricating, patterning and repairing ELMs based on the promising biomaterial of bacterial cellulose.

scholarly journals A Novel and Efficient High-Yield Method for Preparing Bacterial Ghosts

Toxins ◽  
2021 ◽  
Vol 13 (6) ◽  
pp. 420
Author(s):  
Yi Ma ◽  
Liu Cui ◽  
Meng Wang ◽  
Qiuli Sun ◽  
Kaisheng Liu ◽  
...  
Keyword(s):  
Large Scale ◽  
Expression System ◽  
High Yield ◽  
Wild Type ◽  
High Quality ◽  
Efficient Protection ◽  
Bacterial Ghosts ◽  
Cell Envelopes ◽  
Extracellular Structures ◽  
First Time

Bacterial ghosts (BGs) are empty cell envelopes possessing native extracellular structures without a cytoplasm and genetic materials. BGs are proposed to have significant prospects in biomedical research as vaccines or delivery carriers. The applications of BGs are often limited by inefficient bacterial lysis and a low yield. To solve these problems, we compared the lysis efficiency of the wild-type protein E (EW) from phage ΦX174 and the screened mutant protein E (EM) in the Escherichia coli BL21(DE3) strain. The results show that the lysis efficiency mediated by protein EM was improved. The implementation of the pLysS plasmid allowed nearly 100% lysis efficiency, with a high initial cell density as high as OD600 = 2.0, which was higher compared to the commonly used BG preparation method. The results of Western blot analysis and immunofluorescence indicate that the expression level of protein EM was significantly higher than that of the non-pLysS plasmid. High-quality BGs were observed by SEM and TEM. To verify the applicability of this method in other bacteria, the T7 RNA polymerase expression system was successfully constructed in Salmonella enterica (S. Enterica, SE). A pET vector containing EM and pLysS were introduced to obtain high-quality SE ghosts which could provide efficient protection for humans and animals. This paper describes a novel and commonly used method to produce high-quality BGs on a large scale for the first time.

SECONDARY CHANGES IN CARBONATE ROCKS OF OIL AND GAS COMPLEXES

2020 ◽  
pp. 18-23
Author(s):  
M.A. Tugarova
Keyword(s):  
Carbonate Rocks ◽  
Oil And Gas ◽  
Carbonate Reservoirs ◽  
Fundamental Importance ◽  
Schematic Diagram ◽  
Reservoir Properties ◽  
Physico Chemical ◽  
Chemical Conditions ◽  
First Time

The article considers the secondary transformations of carbonate rocks of oil and gas complexes, which are of fundamental importance in the formation of reservoir properties. For the first time, a schematic diagram, illustrating the regularities of secondary processes in carbonate reservoirs and their relationship with the physico-chemical conditions of the stratosphere is proposed.

The Identification and Synthesis of Further Lichen β-Orcinol para-Depsides

1989 ◽  
Vol 42 (7) ◽  
pp. 1191 ◽  
Author(s):  
JA Elix ◽  
DO Chester ◽  
KL Gaul ◽  
JL Parker ◽  
JH Wardlaw
Keyword(s):  
Total Synthesis ◽  
First Time

The new lichen depsides, methyl 5-chloronorobtusatate (4) and 4-O-demethyldiffractaic acid (5), have been detected in an Erioderma sp. And Xanthoparmelia duplicata Hale respectively, and the structures confirmed by total synthesis. In addition, the lichen depsides, 2'-O- methylatranorin (1), 2-O-methylsquamatic acid (2) and elatinic acid (3), have been prepared by unambiguous synthesis for the first time.

scholarly journals Stable and Oriented Liquid Crystal Droplets Stabilized by Imidazolium Ionic Liquids

Molecules ◽  
2021 ◽  
Vol 26 (19) ◽  
pp. 6044
Author(s):  
Efthymia Ramou ◽  
Guilherme Rebordão ◽  
Susana I. C. J. Palma ◽  
Ana C. A. Roque
Keyword(s):  
Ionic Liquids ◽  
Liquid Crystal ◽  
Soft Matter ◽  
Sodium Dodecyl ◽  
High Yield ◽  
Molecular Features ◽  
Surface Active ◽  
State Of Matter ◽  
First Time ◽  
Sds Surfactant

Liquid crystals represent a fascinating intermediate state of matter, with dynamic yet organized molecular features and untapped opportunities in sensing. Several works report the use of liquid crystal droplets formed by microfluidics and stabilized by surfactants such as sodium dodecyl sulfate (SDS). In this work, we explore, for the first time, the potential of surface-active ionic liquids of the imidazolium family as surfactants to generate in high yield, stable and oriented liquid crystal droplets. Our results show that [C12MIM][Cl], in particular, yields stable, uniform and monodisperse droplets (diameter 74 ± 6 µm; PDI = 8%) with the liquid crystal in a radial configuration, even when compared with the standard SDS surfactant. These findings reveal an additional application for ionic liquids in the field of soft matter.

One-step catalytic amination of naphthalene to naphthylamine with exceptional yield

2020 ◽  
Vol 22 (9) ◽  
pp. 2744-2749
Author(s):  
Fang Hao ◽  
Xin Wang ◽  
Linfang Huang ◽  
Wei Xiong ◽  
Pingle Liu ◽  
...  
Keyword(s):  
Mild Condition ◽  
Major Product ◽  
High Yield ◽  
Vanadium Catalysts ◽  
Catalytic Amination ◽  
One Step ◽  
First Time

This is the first time to synthesize naphthylamine from one-step naphthalene amination by vanadium catalysts with high yield under mild condition. It could obtain ∼70% yield of naphthylamine, with major product of valuable 1,5-diaminonaphthalene.

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