Beyond conventional construction of phthalimide core: A review

2021 ◽  
Author(s):  
Suven Das
Keyword(s):  
Natural Products ◽  
Organic Materials ◽  
Structural Motif ◽  
Primary Amines ◽  
Common Strategy ◽  
Phthalic Acids

Phthalimides are privileged structural motif frequently found in natural products, pharmaceuticals and organic materials. The Most common strategy for their synthesis involves condensation of phthalic acids/anhydrides with primary amines. However,...

A general metal-free route towards the synthesis of 1,2,3-triazoles from readily available primary amines and ketones

2016 ◽  
Vol 52 (14) ◽  
pp. 2885-2888 ◽  
Author(s):  
Joice Thomas ◽  
Sampad Jana ◽  
Jubi John ◽  
Sandra Liekens ◽  
Wim Dehaen
Keyword(s):  
Natural Products ◽  
Primary Amines ◽  
Metal Free ◽  
Amino Esters

A metal-free route towards different 1,2,3-triazole heterocycles was accomplished by using inexpensive and readily available ketones and primary amines. This reaction is very general and was extended to functionalize different amino esters, dendrimers and natural products.

Biosynthesis of cyclopropane in natural products

2022 ◽  
Author(s):  
Suze Ma ◽  
Dhanaraju Mandalapu ◽  
Shu Wang ◽  
Qi Zhang
Keyword(s):  
Natural Products ◽  
Biochemical Properties ◽  
Structural Motif ◽  
Enzymatic Pathways

This review discusses the diverse enzymatic pathways in the biosynthesis of cyclopropane, a unique structural motif with important biochemical properties.

Total Synthesis of the Pseudoindoxyl Class of Natural Products

2021 ◽  
Author(s):  
Pawan Surendra Dhote ◽  
Pitambar Patel ◽  
Kumar Vanka ◽  
Chepuri Ramana
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Structural Motif ◽  
Large Set

The pseudoindoxyl sub-structural motif, amongst the large set of the indole class of alkaloids, represents a unique subset of the oxygenated indole class of the alkaloids family. A majority of...

scholarly journals Biosynthesis of sulfonamide and sulfamate antibiotics in Actinomycete

2021 ◽  
Author(s):  
Takayoshi Awakawa ◽  
Lena Barra ◽  
Ikuro Abe
Keyword(s):  
Natural Products ◽  
Second Generation ◽  
Structural Motif ◽  
Organosulfur Compounds ◽  
Antibacterial Drugs ◽  
Structural Motifs ◽  
Detailed Understanding ◽  
Bacterial Genus ◽  
Current State ◽  
Biosynthetic Engineering

Abstract Sulfonamides and sulfamates are a group of organosulfur compounds that contain the signature sulfamoyl structural motif. These compounds were initially only known as synthetic antibacterial drugs but were later also discovered as natural products. Eight highly potent examples have been isolated from actinomycetes to date, illustrating the large biosynthetic repertoire of this bacterial genus. For the biosynthesis of these compounds, several distinct and unique biosynthetic machineries have been discovered, capable to generate the unique S-N bond. For the creation of novel, second generation natural products by biosynthetic engineering efforts, a detailed understanding of the underlying enzyme machinery towards potent structural motifs is crucial. In this review, we aim to summarize the current state of knowledge on sulfonamide and sulfamate biosynthesis. A detailed discussion for the secondary sulfamate ascamycin, the tertiary sulfonamide sulfadixiamycin A, and the secondary sulfonamide SB-203208 is provided and their bioactivities and mode of actions are discussed.

scholarly journals Recent Advances in the Synthesis of Isothiocyanates Using Elemental Sulfur

Catalysts ◽  
2021 ◽  
Vol 11 (9) ◽  
pp. 1081
Author(s):  
András Gy. Németh ◽  
Péter Ábrányi-Balogh
Keyword(s):  
Natural Products ◽  
Best Practices ◽  
Organic Synthesis ◽  
Elemental Sulfur ◽  
Biologically Active ◽  
Primary Amines ◽  
Pharmaceutical Ingredients ◽  
Recent Developments ◽  
In Situ Generation

Isothiocyanates (ITCs) are biologically active molecules found in several natural products and pharmaceutical ingredients. Moreover, due to their high and versatile reactivity, they are widely used as intermediates in organic synthesis. This review considers the best practices for the synthesis of ITCs using elemental sulfur, highlighting recent developments. First, we summarize the in situ generation of thiocarbonyl surrogates followed by their transformation in the presence of primary amines leading to ITCs. Second, carbenes and amines afford isocyanides, and the further reaction of this species with sulfur readily generates ITCs under thermal, catalytic or basic conditions. Additionally, we also reveal that in the catalyst-free reaction of isocyanides and sulfur, two—until this time overlooked and not investigated—different mechanistic pathways exist.

Synthesis of Thioethers from Sulfonyl Chlorides, Sodium Sulfinates, and Sulfonyl Hydrazides

Synthesis ◽  
2019 ◽  
Vol 51 (19) ◽  
pp. 3567-3587 ◽  
Author(s):  
Ronghai Wu ◽  
Keke Huang ◽  
Guanyinsheng Qiu ◽  
Jin-Biao Liu
Keyword(s):  
Natural Products ◽  
Organic Materials ◽  
Pharmaceutical Compounds ◽  
Sulfonyl Chlorides ◽  
Different Types ◽  
Sulfur Containing ◽  
The Ideal

Sulfur-containing moieties, especially thioethers (sulfides), play pivotal roles in the functionalities of many natural products, pharmaceutical compounds, and organic materials. In this review, we summarize the recent synthetic protocols of thioethers using thiolating reagents, including sulfonyl chlorides, sodium sulfinates, and sulfonyl hydrazides, as the ideal starting materials. Representative mechanisms for different types of reaction are also discussed.1 Introduction2 Synthesis of Thioethers from Sulfonyl Chlorides3 Synthesis of Thioethers from Sodium Sulfinates4 Synthesis of Thioethers from Sulfonyl Hydrazides5 Conclusion

Unconventional Approaches for the Introduction of Sulfur-based Functional Groups

2021 ◽  
Author(s):  
Alberto Lanfranco ◽  
Riccardo Moro ◽  
Emanuele Azzi ◽  
Annamaria Deagostino ◽  
Polyssena Renzi
Keyword(s):  
Natural Products ◽  
Functional Groups ◽  
Organic Materials ◽  
Pivotal Role ◽  
Organosulfur Compounds ◽  
New Methodologies

Organosulfur compounds have a pivotal role in the functionalities of many natural products, pharmaceuticals and organic materials. For these reason, the search for new methodologies for the formation of carbon–sulfur...

scholarly journals Bioinspired Syntheses of Herqulines B and C from Cyclodipeptide Mycocyclosin

2018 ◽  
Author(s):  
Xu Zhu ◽  
Christopher C. McAtee ◽  
Corinna Schindler
Keyword(s):  
Natural Products ◽  
Oxidation State ◽  
Structural Motif ◽  
Hypervalent Iodine ◽  
Birch Reduction ◽  
System Characteristic

<div>A bioinspired approach for the syntheses of herqulines B and C is reported that takes advantage of an Ltyrosine-derived diketopiperazine, a mycocyclosin analog, as a synthetic precursor. The strategy relies on a series of consecutive reductions to adjust the mycocyclosin oxidation state to that observed in the herquline class of natural products. The strained and distorted L-tyrosine-based biaryl system characteristic for mycocyclosin is selectively converted to the 1,4-diketone structural motif common to the herqulines via initial hypervalent iodine-mediated dearomatization and a subsequent directed Birch reduction, enabled by an intramolecular H-source. The piperazine oxidation state is accessible in an iron-catalyzed reduction of the diketopiperazine precursor.</div>

scholarly journals A General Approach to 2,2-Disubstituted Indoxyls: Total Synthesis of Brevianamide A and Trigonoliimine C

2021 ◽  
Author(s):  
Fan Xu ◽  
Myles Smith
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Bioactive Compounds ◽  
Structural Motif ◽  
Total Syntheses ◽  
Broad Scope ◽  
Nucleophilic Trapping ◽  
General Method

The indoxyl unit is a common structural motif in alkaloid natural products and bioactive compounds. Here, we report a general method that transforms readily available 2-substituted indoles into 2,2-disubstituted indoxyls via nucleophile coupling with a 2-alkoxyindoxyl intermediate and showcase its utility in short total syntheses of the alkaloids brevianamide A (7 steps) and trigonoliimine C (6 steps). The developed method is operationally simple and demonstrates broad scope in terms of nucleophile identity and indole substitution, tolerating 2-alkyl substituents and free indole N–H groups, elements beyond the scope of most prior approaches. Spirocyclic indoxyl products are also accessible via intramolecular nucleophilic trapping.

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