scholarly journals A chromatography-free total synthesis of a ferrocene-containing dendrimer exhibiting the property to recognize 9,10-diphenylantracene

2021 ◽  
Author(s):  
Artur Kasprzak ◽  
Monika K. Nisiewicz ◽  
Anna Maria Nowicka
Keyword(s):  
Total Synthesis ◽  
Target Compound

Molecules comprising several ferrocene residues constitute an intriguing group of compounds for various applications. Here, the total synthesis of a new example of ferrocene-containing dendrimer is presented. The target compound...

First Total Synthesis of a Fluorinated Calystegin

2010 ◽  
Vol 65 (4) ◽  
pp. 445-451 ◽  
Author(s):  
René Csuk ◽  
Erik Prell ◽  
Stefan Reißmann ◽  
Claudia Korb
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Competitive Inhibitor ◽  
Ring Closure ◽  
Target Compound ◽  
Metathesis Reaction ◽  
Grubbs Catalyst ◽  
Ring Opening Reaction ◽  
Ultrasound Assisted ◽  
Key Steps

A straightforward chiral pool synthesis for the first fluorinated calystegin is described. Key steps of this synthesis include an ultrasound-assisted Zn-mediated tandem ring opening reaction followed by a Grubbs’ catalyst-mediated ring closure metathesis reaction. The target compound is a selective and competitive inhibitor for a β -glycosidase.

scholarly journals Total Synthesis of the Reported Structure of Cahuitamycin A

2020 ◽  
Author(s):  
Justin Shapiro ◽  
Savannah Post ◽  
William Wuest
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Twelve Step ◽  
Target Compound ◽  
New Family ◽  
Iron Trafficking ◽  
Linear Sequence ◽  
Alternative Structure ◽  
Synthetic Target

In a 2016 screen of natural product extracts a new family of natural products, the cahuitamycins, was discovered and found to inhibit the formation of biofilms in the human pathogen <i>Acinetobacter baumannii</i>. The molecules contain an unusual piperazate residue that raises structure/function and biosynthesis questions and resemble iron-trafficking virulence factors from <i>A. baumannii</i>, suggesting a connection between metal homeostasis and biofilm-mediated pathogenicity. Here we disclose the first total synthesis of the reported structure of cahuitamycin A in a twelve-step longest linear sequence and 18% overall yield. Comparison of spectral data of the authentic natural product and synthetic target compound demonstrate that the reported structure is distinct from the isolated metabolite. Herein, we propose an alternative structure to reconcile our findings with the isolation report, setting the stage for future synthetic and biochemical investigations of an important class of natural products.

Synthesis of plantamajoside, a bioactive dihydroxyphenylethyl glycoside from Plantago major L.

Holzforschung ◽  
2006 ◽  
Vol 60 (5) ◽  
pp. 492-497 ◽  
Author(s):  
Toshinari Kawada ◽  
Yuko Yoneda ◽  
Ryuji Asano ◽  
Ippei Kan-no ◽  
Walther Schmid
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Total Synthesis ◽  
Caffeic Acid ◽  
Spectral Data ◽  
Natural Compound ◽  
Plantago Major ◽  
Target Compound ◽  
Sugar Esters ◽  
Nuclear Magnetic

Abstract The first total synthesis of plantamajoside (1), 2-(3′,4′-dihydroxylphenyl)ethyl-4-O-caffeoyl-3-O-(β-D-glucopyranosyl)-β-D-glucopyranoside, which is one of the dihydroxyphenylethyl glycosides (caffeic acid sugar esters), is described. Key intermediate 2, 2-[3′,4′-bis(O-benzyl)phenyl]ethyl 2,6-di-O-acetyl-4-O-[3′,4′-bis(O-benzyl)caffeoyl]-β-D-glucopyranoside was glycosylated with trichloroacetoimidoyl 2,3,4,6-tetra-O-acetyl-α-D-glycopyranoside (3) to afford plantamajoside derivative 4a, 2-[3′,4′-bis(O-benzyl)phenyl]ethyl 2,6-di-O-acetyl-4-O-[3′,4′-bis(O-benzyl)caffeoyl]-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside, in 39% yield. Plantamajoside derivative 4a was successfully converted into the target compound, plantamajoside (1), through a series of de-protective procedures. 1H- and 13C nuclear magnetic resonance (NMR) spectral data of the synthesized plantamajoside (1) were identical to those of the natural compound.

Total synthesis of (+)-thromboxane B2 from D-glucose. A detailed account

1981 ◽  
Vol 59 (5) ◽  
pp. 870-877 ◽  
Author(s):  
Stephen Hanessian ◽  
Pierre Lavallee
Keyword(s):  
Total Synthesis ◽  
Thromboxane B2 ◽  
Detailed Account ◽  
Target Compound ◽  
Type Symmetry

The total synthesis of thromboxane B2 from D-glucose is described, based on the recognition of hidden carbohydrate-type symmetry in the molecule. Methyl 2-deoxy-α-D-ribo-hexopyranoside was prepared from D-glucose and manipulated in such a way as to introduce C-branching at C-4 in a stereocontrolled manner. This crucial intermediate was then transformed into the target compound by adaptations of established methodology in the field.

scholarly journals Total Synthesis of the Reported Structure of Cahuitamycin A

2020 ◽  
Author(s):  
Justin Shapiro ◽  
Savannah Post ◽  
William Wuest
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Twelve Step ◽  
Target Compound ◽  
New Family ◽  
Iron Trafficking ◽  
Linear Sequence ◽  
Alternative Structure ◽  
Synthetic Target

In a 2016 screen of natural product extracts a new family of natural products, the cahuitamycins, was discovered and found to inhibit the formation of biofilms in the human pathogen <i>Acinetobacter baumannii</i>. The molecules contain an unusual piperazate residue that raises structure/function and biosynthesis questions and resemble iron-trafficking virulence factors from <i>A. baumannii</i>, suggesting a connection between metal homeostasis and biofilm-mediated pathogenicity. Here we disclose the first total synthesis of the reported structure of cahuitamycin A in a twelve-step longest linear sequence and 18% overall yield. Comparison of spectral data of the authentic natural product and synthetic target compound demonstrate that the reported structure is distinct from the isolated metabolite. Herein, we propose an alternative structure to reconcile our findings with the isolation report, setting the stage for future synthetic and biochemical investigations of an important class of natural products.

Synthesis of 2,6-dimethoxy-9-phenyl-1H-phenalen-1-one and structural revision of the benzoindenone from Eichhornia crassipes

2019 ◽  
Vol 74 (2) ◽  
pp. 183-189
Author(s):  
Xiaowan Li ◽  
Tongxu Si ◽  
Chuenfai Ku ◽  
Hongjie Zhang ◽  
Mingzhong Wang ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Total Synthesis ◽  
Eichhornia Crassipes ◽  
Target Compound ◽  
Structural Revision ◽  
Synthetic Strategy ◽  
Nmr Data

AbstractThe total synthesis of the natural phytoalexin 2,6-dimethoxy-9-phenyl-1H-phenalen-1-one (3) isolated from Eichhornia crassipes was accomplished in seven steps. The synthetic strategy included a Friedel–Crafts acylation and a Jacobsen–Katsuki epoxidation as the key reactions to obtain the target compound. Based on a comparison of the NMR data and a crystal structure of 3, the previously proposed structure of 2,5-dimethoxy-4-phenyl-benzoindenone (2) isolated from the same plant has been revised.

scholarly journals The Serendipitous Discovery of a Rose Odorant

2020 ◽  
Vol 74 (4) ◽  
pp. 247-251
Author(s):  
Nicole Hauser ◽  
Philip Kraft ◽  
Erick M. Carreira
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Small Molecule ◽  
First Generation ◽  
Scientific Research ◽  
Careful Analysis ◽  
Target Compound ◽  
Electrically Conductive ◽  
New Approaches ◽  
Expected Outcome

Serendipity has played a role in many groundbreaking scientific discoveries. Key to their identification and exploitation is the ability to recognize the unexpected and invest time trying to understand it. Like any other field of scientific research, total synthesis requires determination and perseverance. When the first-generation route towards a target compound fails, new approaches are developed based on insights gained in the initial studies. Careful analysis of data obtained in a 'failed' approach, e.g. when a reaction did not yield the desired or any expected outcome, can lead to spectacularly improved routes and discoveries that have impact beyond the synthesis of the selected target compound. Serendipity has further led to the identification of intriguing properties that materials or single molecules have, as exemplified by the discovery of electrically conductive polymers. During our total synthesis endeavors towards a complex natural product, we identified a small molecule with interesting olfactory properties, which we decided to investigate further.

First Total Synthesis of 3-Epi-calystegin B2

2011 ◽  
Vol 66 (3) ◽  
pp. 317-323
Author(s):  
René Csuk ◽  
Stefan Reißmann ◽  
Ralph Kluge ◽  
Dieter Ströhl ◽  
Claudia Korb
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Tight Binding ◽  
Ring Closure ◽  
Hydroxyl Group ◽  
Target Compound ◽  
Metathesis Reaction ◽  
Ring Opening Reaction ◽  
Ultrasound Assisted ◽  
Key Steps

A straightforward chiral pool synthesis for a non-natural calystegin, 3-epi-B2, is described. Key steps of this synthesis include an ultrasound-assisted Zn-mediated tandem ring opening reaction followed by a Grubbs’ catalyst-mediated ring closure metathesis reaction. Compared to calystegin B2, the target compound is no longer an inhibitor for a β -glycosidase hence proving that an equatorial hydroxyl group at position C-3 is necessary for a tight binding of calystegins into the active site of β -glycosidases.

scholarly journals Total Synthesis of Natural Disaccharide Sambubiose

2020 ◽  
Vol 13 (8) ◽  
pp. 198
Author(s):  
Simone Lucarini ◽  
Maria Gessica Ciulla ◽  
Paola Mestichelli ◽  
Andrea Duranti
Keyword(s):  
Total Synthesis ◽  
Synthetic Method ◽  
Target Compound ◽  
Single Isomer

A practical and robust synthetic method to obtain the natural disaccharide sambubiose (2-O-β-D-xylopyranosyl-D-glucopyranose) is reported, exploring the key step in the synthesis, i.e., stereoselective O-glycosylation. Specifically, the best combinations of glycoside donors and acceptors were identified, stereospecific control of the reaction was achieved by screening several catalysts and protection/deprotection steps were evaluated and improved. The best result was obtained by coupling allyl 3,5,6-tri-O-benzyl-β-D-glucofuranoside with 2,3,4-tri-O-acetyl-D-xylopiranosyl-α-trichloro acetimidate in the presence of trimethylsilyl triflate as a catalyst giving the corresponding protected target compound as a correct single isomer. The latter was transformed accordingly into the desired final product by deprotection steps (deallylation, deacetylation, and debenzylation). Sambubiose was synthesized into a satisfactory and higher overall yield than previously reported and was also characterized.

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