Total synthesis of tricolorin A via interrupted Pummerer reaction-mediated glycosylation and one-pot relay glycosylation

2020 ◽  
Vol 18 (20) ◽  
pp. 3818-3822
Author(s):  
Jiuchang Sun ◽  
Jing Fang ◽  
Xiong Xiao ◽  
Lei Cai ◽  
Xiang Zhao ◽  
...  
Keyword(s):  
Total Synthesis ◽  
High Efficiency ◽  
One Pot ◽  
Pummerer Reaction

The total synthesis of tricolorin A was achieved with high efficiency based on interrupted Pummerer reaction-mediated (IPRm) glycosylation and one-pot relay glycosylation.

A One-Pot Chemoenzymatic Synthesis of (2S,4R)-4-Methylproline Enables the First Total Synthesis of Antiviral Lipopeptide Cavinafungin B

2018 ◽  
Author(s):  
Christian R. Zwick ◽  
Hans Renata
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Complex Molecule ◽  
Molecular Target ◽  
Chemoenzymatic Synthesis ◽  
General Strategy ◽  
One Pot

We report an efficient ten-step synthesis of antiviral natural product cavinafungin B in 37% overall yield. By leveraging a one-pot chemoenzymatic synthesis of (2S,4R)-4-methylproline and oxazolidine-tethered (Rink-Boc-ATG-resin) SPPS methodology, the assembly of our molecular target could be conducted in an efficient manner.This general strategy could prove amenable to the construction of other natural and unnatural linear lipopeptides. The value of incorporating biocatalytic steps in complex molecule synthesis is highlighted by this work.

Metal-Free Photoredox-Catalyzed C–H/C–H Coupling of Arenes Enabled by Interrupted Pummerer Activation

2019 ◽  
Author(s):  
Miles Aukland ◽  
Mindaugas Šiaučiulis ◽  
Adam West ◽  
Gregory Perry ◽  
David Procter
Keyword(s):  
Natural Product ◽  
Selective Reduction ◽  
Cross Coupling ◽  
One Pot ◽  
Complex Molecules ◽  
Pummerer Reaction ◽  
Metal Free ◽  
Bond Forming ◽  
Coupling Partner ◽  
Bioactive Natural Product

<p>Aryl–aryl cross-coupling constitutes one of the most widely used procedures for the synthesis of high-value materials, ranging from pharmaceuticals to organic electronics and conducting polymers. The assembly of (hetero)biaryl scaffolds generally requires multiple steps; coupling partners must be functionalized before the key bond-forming event is considered. Thus, the development of selective C–H arylation processes in arenes, that side-step the need for prefunctionalized partners, is crucial for streamlining the construction of these key architectures. Here we report an expedient, one-pot assembly of (hetero)biaryl motifs using photocatalysis and two non-prefunctionalized arene partners. The approach is underpinned by the activation of a C–H bond in an arene coupling partner using the interrupted Pummerer reaction. A unique pairing of the organic photoredox catalyst and the intermediate dibenzothiophenium salts enables highly selective reduction in the presence of sensitive functionalities. The utility of the metal-free, one-pot strategy is exemplified by the synthesis of a bioactive natural product and the modification of complex molecules of societal importance.</p>

Chlorosulfonic Acid Supported Piperidine-4-carboxylic Acid (PPCA) Functionalized Fe3O4 Nanoparticles (Fe3O4-PPCA): The Efficient, Green and Reusable Nanocatalyst for the Synthesis of Pyrazolyl Coumarin Derivatives under Solvent-Free Conditions

2019 ◽  
Vol 22 (2) ◽  
pp. 123-128
Author(s):  
Setareh Habibzadeh ◽  
Hassan Ghasemnejad-Bosra ◽  
Mina Haghdadi ◽  
Soheila Heydari-Parastar
Keyword(s):  
Carboxylic Acid ◽  
Fe3o4 Nanoparticles ◽  
High Efficiency ◽  
Reaction Times ◽  
Chlorosulfonic Acid ◽  
Aromatic Aldehydes ◽  
Solvent Free ◽  
Magnetic Nanocatalyst ◽  
One Pot ◽  
Solvent Free Conditions

Background: In this study, we developed a convenient methodology for the synthesis of coumarin linked to pyrazolines and pyrano [2,3-h] coumarins linked to 3-(1,5-diphenyl-4,5- dihydro-1H-pyrazol-3-yl)-chromen-2-one derivatives using Chlorosulfonic acid supported Piperidine-4-carboxylic acid (PPCA) functionalized Fe3O4 nanoparticles (Fe3O4-PPCA) catalyst. Materials and Methods:: Fe3O4-PPCA was investigated as an efficient and magnetically recoverable Nanocatalyst for the one-pot synthesis of substituted coumarins from the reaction of coumarin with a variety of aromatic aldehydes in high to excellent yield at room temperature under solvent-free conditions. The magnetic nanocatalyst can be easily recovered by applying an external magnet device and reused for at least 10 reaction runs without considerable loss of reactivity. Results and Conclusion: The advantages of this protocol are the use of commercially available materials, simple and an inexpensive procedure, easy separation, and an eco-friendly procedure, and it shows good reaction times, good to high yields, inexpensive and practicability procedure, and high efficiency.

Fast and high-efficiency synthesis of 2-substituted benzothiazoles via combining enzyme catalysis and photoredox catalysis in one-pot

2020 ◽  
pp. 104607
Author(s):  
Zeng-Jie Yang ◽  
Qing-Tian Gong ◽  
Yuan Yu ◽  
Wei-Fan Lu ◽  
Zhe-Ning Wu ◽  
...  
Keyword(s):  
Enzyme Catalysis ◽  
High Efficiency ◽  
Photoredox Catalysis ◽  
One Pot

First total synthesis of oteromycin utilizing one-pot four-step cascade reaction strategy

2013 ◽  
Vol 54 (6) ◽  
pp. 506-511 ◽  
Author(s):  
Hiromi Uchiro ◽  
Nobuhiro Shionozaki ◽  
Ryo Tanaka ◽  
Hiroyuki Kitano ◽  
Naoki Iwamura ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Cascade Reaction ◽  
One Pot

ChemInform Abstract: A One-Pot Preparation of Aryl- and Heteroarylcycloalkenes: Application to the Total Synthesis of (.+-.)-Laurokamurene B.

ChemInform ◽  
2010 ◽  
Vol 41 (9) ◽  
Author(s):  
Jean Tallineau ◽  
Georges Bashiardes ◽  
Jean-Marie Coustard ◽  
Frederic Lecornue
Keyword(s):  
Total Synthesis ◽  
One Pot

A One-Pot Preparation of Aryl- and Heteroarylcycloalkenes: Application to the Total Synthesis of (±)-Laurokamurene B

Synlett ◽  
2009 ◽  
Vol 2009 (17) ◽  
pp. 2761-2764 ◽  
Author(s):  
Frédéric Lecornué ◽  
Jean Tallineau ◽  
Georges Bashiardes ◽  
Jean-Marie Coustard
Keyword(s):  
Total Synthesis ◽  
One Pot

Total Synthesis of (−)-Hippodamine by Stereocontrolled Construction of Azaphenalene Skeleton Based on Extended One-Pot Asymmetric Azaelectrocyclization

2013 ◽  
Vol 15 (11) ◽  
pp. 2758-2761 ◽  
Author(s):  
Shintaro Fujita ◽  
Taku Sakaguchi ◽  
Toyoharu Kobayashi ◽  
Hiroshi Tsuchikawa ◽  
Shigeo Katsumura
Keyword(s):  
Total Synthesis ◽  
One Pot
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