scholarly journals A Practical, Component-Based Synthetic Route to Methylthiolincosamine Permitting Facile Northern-Half Diversification of Lincosamide Antibiotics

2021 ◽  
Author(s):  
Matthew Mitcheltree ◽  
Jack W. Stevenson ◽  
Amarnath Pisipati ◽  
Andrew G. Myers
Keyword(s):  
Late Stage ◽  
Building Block ◽  
Synthetic Route ◽  
Northern Half ◽  
Glycosyl Donor ◽  
Flexible Component

The development of a flexible, component-based synthetic route to the aminosugar fragment of the lincosamide antibiotics is described. This synthetic route hinges on the application and extension of nitroaldol chemistry to forge strategic bonds within complex aminosugar targets, and employs a glycal epoxide as a versatile glycosyl donor for the installation of various anomeric groups. Through building-block exchange and late-stage functionalization, this route affords access to a host of rationally designed lincosamides otherwise inaccessible by semisynthesis, and underpins a platform for the discovery of new lincosamide antibiotics.

scholarly journals A Practical, Component-Based Synthetic Route to Methylthiolincosamine Permitting Facile Northern-Half Diversification of Lincosamide Antibiotics

2021 ◽  
Author(s):  
Matthew Mitcheltree ◽  
Jack W. Stevenson ◽  
Amarnath Pisipati ◽  
Andrew G. Myers
Keyword(s):  
Late Stage ◽  
Building Block ◽  
Synthetic Route ◽  
Northern Half ◽  
Glycosyl Donor ◽  
Flexible Component

The development of a flexible, component-based synthetic route to the aminosugar fragment of the lincosamide antibiotics is described. This synthetic route hinges on the application and extension of nitroaldol chemistry to forge strategic bonds within complex aminosugar targets, and employs a glycal epoxide as a versatile glycosyl donor for the installation of various anomeric groups. Through building-block exchange and late-stage functionalization, this route affords access to a host of rationally designed lincosamides otherwise inaccessible by semisynthesis, and underpins a platform for the discovery of new lincosamide antibiotics.

Synthesis and characterization of a series of novel phenol- and polyphenol-based glycerolipids

2006 ◽  
Vol 84 (10) ◽  
pp. 1411-1415 ◽  
Author(s):  
Rolf Schmidt ◽  
Joseph G Carrigan ◽  
Christine E DeWolf
Keyword(s):  
Hydrogen Bonding ◽  
Chain Length ◽  
Protein Interaction ◽  
Building Block ◽  
Synthesis And Characterization ◽  
Synthetic Route ◽  
Substitution Pattern ◽  
Lipid Protein Interaction ◽  
Block Approach

A building block approach was used to design a modular synthetic route for the preparation of novel glycerolipids with phenolic and polyphenolic headgroups. Based on this scheme, it is possible to vary the substitution pattern of the headgroup, the stereochemistry of the backbone, and the length of the sidechains. Five glycerolipids with different headgroups and identical backbone stereochemistry and chain length have been prepared.Key words: glycerolipid, polyphenol, hydrogen bonding, lipid-protein interaction, self-adhering.

scholarly journals Carbon isotope labeling of carbamates by late-stage [11C], [13C] and [14C]carbon dioxide incorporation

2020 ◽  
Vol 56 (78) ◽  
pp. 11677-11680
Author(s):  
Antonio Del Vecchio ◽  
Alex Talbot ◽  
Fabien Caillé ◽  
Arnaud Chevalier ◽  
Antoine Sallustrau ◽  
...  
Keyword(s):  
Carbon Dioxide ◽  
Carbon Isotope ◽  
Carbon Isotopes ◽  
Late Stage ◽  
Building Block ◽  
Isotope Labeling

A procedure which allows labelling cyclic carbamates with all carbon isotopes has been developed. This protocol valorizes carbon dioxide, the universal building block for radiolabeling. A series of pharmaceuticals were obtained and a disconnection/reconnection strategy was implemented.

Total Synthesis of (–)-Aristoquinoline via an Intramolecular Nitrilium Ion Cyclization

Synthesis ◽  
2021 ◽  
Author(s):  
Keith P. Reber ◽  
Priyansh D. Gujarati
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Building Block ◽  
Spectroscopic Properties ◽  
Ring System ◽  
Synthetic Route ◽  
Enantioselective Total Synthesis ◽  
Key Steps

AbstractThe enantioselective total synthesis of the alkaloid aristoquinoline has been achieved in seven steps and 26% overall yield. A new preparation of the useful synthetic building block (–)-α-terpinyl amine was also developed in order to avoid stoichiometric mercury reagents or azide-containing intermediates. Key steps in the optimized synthetic route include an intramolecular nitrilium ion cyclization to form the characteristic azabicyclo[3.3.1]nonane ring system and a dia­stereoselective reduction of the resulting imine mixture to afford the natural product. An isomer of aristoquinoline containing an exocyclic alkene was also obtained and found to exhibit unusual chromatographic and spectroscopic properties.

scholarly journals Exploration of new reaction tools for late-stage functionalization of complex chemicals

2019 ◽  
Vol 97 (2) ◽  
pp. 67-85 ◽  
Author(s):  
Alejandra Dominguez-Huerta ◽  
Xi-Jie Dai ◽  
Feng Zhou ◽  
Pierre Querard ◽  
Zihang Qiu ◽  
...  
Keyword(s):  
Environmental Impact ◽  
Late Stage ◽  
Chemical Transformations ◽  
Synthetic Route ◽  
Atom Economy ◽  
Complex Molecules ◽  
Mild Conditions ◽  
The Past ◽  
Renewable Feedstocks ◽  
Selective Chemical

Chemistry has always had as a target the conversion of molecules into valuable materials. Nevertheless, the aim of past synthesis has primarily focused on achieving a given transformation, regardless of the environmental impact of the synthetic route. Given the current global situation, the demand for sustainable alternatives has substantially increased. Our group focuses on developing selective chemical transformations that benefit from mild conditions, improved atom economy, and that can make use of renewable feedstocks as starting materials. This account summarizes our work over the past two decades specifically regarding the selective removal, conversion, and addition of functional groups that can, later on, be applied at a late stage for the modification of complex molecules.

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.

A concise synthesis of the O-glycosylated amino acid building block; using phenyl selenoglycoside as a glycosyl donor

2000 ◽  
Vol 41 (17) ◽  
pp. 3127-3130 ◽  
Author(s):  
Weir-Torn Jiaang ◽  
Meng-Yang Chang ◽  
Ping-Hui Tseng ◽  
Shui-Tein Chen
Keyword(s):  
Amino Acid ◽  
Building Block ◽  
Glycosyl Donor

Synthesis of (±)-γ-Lycorane by Using an Intramolecular Friedel–Crafts Reaction

Synthesis ◽  
2017 ◽  
Vol 49 (20) ◽  
pp. 4711-4716 ◽  
Author(s):  
Bao Doan ◽  
Xin Tan ◽  
Chin Ang ◽  
Roderick Bates
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Building Block ◽  
Diastereoselective Hydrogenation

A total synthesis of γ-lycorane has been achieved by employing N-tosylpyrrole as a key building block. The synthesis employs both an intermolecular and an intramolecular Friedel–Crafts reaction, as well as a completely diastereoselective hydrogenation of a late-stage pyrrole intermediate.

scholarly journals Automated glycan assembly of aS. pneumoniaeserotype 3 CPS antigen

2016 ◽  
Vol 12 ◽  
pp. 1440-1446 ◽  
Author(s):  
Markus W Weishaupt ◽  
Stefan Matthies ◽  
Mattan Hurevich ◽  
Claney L Pereira ◽  
Heung Sik Hahm ◽  
...  
Keyword(s):  
Process Improvement ◽  
Late Stage ◽  
Building Block ◽  
Bacterial Infections ◽  
Capsular Polysaccharide ◽  
Glucuronic Acid ◽  
Severe Disease ◽  
Building Blocks ◽  
Oxidation Step ◽  
Chain Lengths

Vaccines againstS. pneumoniae, one of the most prevalent bacterial infections causing severe disease, rely on isolated capsular polysaccharide (CPS) that are conjugated to proteins. Such isolates contain a heterogeneous oligosaccharide mixture of different chain lengths and frame shifts. Access to defined syntheticS. pneumoniaeCPS structures is desirable. Known syntheses ofS. pneumoniaeserotype 3 CPS rely on a time-consuming and low-yielding late-stage oxidation step, or use disaccharide building blocks which limits variability. Herein, we report the first iterative automated glycan assembly (AGA) of a conjugation-readyS. pneumoniaeserotype 3 CPS trisaccharide. This oligosaccharide was assembled using a novel glucuronic acid building block to circumvent the need for a late-stage oxidation. The introduction of a washing step with the activator prior to each glycosylation cycle greatly increased the yields by neutralizing any residual base from deprotection steps in the synthetic cycle. This process improvement is applicable to AGA of many other oligosaccharides.

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