Recent advances in the Overman rearrangement: synthesis of natural products and valuable compounds

2017 ◽  
Vol 15 (13) ◽  
pp. 2672-2710 ◽  
Author(s):  
Rodney A. Fernandes ◽  
Pullaiah Kattanguru ◽  
Sachin P. Gholap ◽  
Dipali A. Chaudhari
Keyword(s):  
Natural Products ◽  
Building Blocks ◽  
Bond Forming ◽  
Recent Advances ◽  
Synthetic Intermediates ◽  
Valuable Compounds

This review documents the reports since 2005 on the Overman rearrangement, an important C–N bond forming reaction that has been profoundly used in the synthesis of natural products, synthetic intermediates, building blocks and valuable compounds.

scholarly journals Recent Advances in Organocatalyzed Asymmetric Synthesis of Benzopyran and Benzodihydropyran (Chromane) Nuclei

Symmetry ◽  
2019 ◽  
Vol 11 (12) ◽  
pp. 1510
Author(s):  
Renato Dalpozzo ◽  
Raffaella Mancuso
Keyword(s):  
Natural Products ◽  
Asymmetric Synthesis ◽  
Organic Synthesis ◽  
Building Blocks ◽  
Core Structure ◽  
The Core ◽  
Recent Advances ◽  
Set Up

Benzopyran and benzodihydropyran (chromane) nuclei are the core structure of many natural products, in particular flavonoids. Many compounds possessing this structure are nutraceuticals, pharmaceutical nutrients. Therefore, benzopyran and chromane scaffolds are important building blocks in organic synthesis and many efforts have been made to set up efficient methods for their synthesis. In particular, asymmetric methods are of great importance, being natural products, and generally chiral substances. This review aims to cover literature in the range 2017–first half of 2019.

Recent advances of chromone-based reactants in the catalytic asymmetric domino annulation reaction

2021 ◽  
Author(s):  
Min Zhang ◽  
Ying Gong ◽  
Wei Zhou ◽  
Ying Zhou ◽  
Xiong-Li Liu
Keyword(s):  
Natural Products ◽  
Building Blocks ◽  
Bioactive Molecules ◽  
The Core ◽  
Recent Advances ◽  
Catalytic Asymmetric

Chiral polycyclic chromanones are important heterocyclic frameworks that constitute the core structures of many natural products and bioactive molecules. As starting materials, the chromone-based reactants are very efficient building blocks...

Recent advances for the synthesis of chiral sulfones with the sulfone moiety directly connected to the chiral center

2021 ◽  
Author(s):  
Chuanle Zhu ◽  
Yingying Cai ◽  
Huanfeng Jiang
Keyword(s):  
Natural Products ◽  
Bioactive Compounds ◽  
Building Blocks ◽  
Chiral Center ◽  
Recent Advances ◽  
Chiral Centers

Chiral sulfones, especially for those compounds with the sulfone groups directly connected to the chiral centers, are privileged building blocks in many natural products and bioactive compounds. Thus, the development...

scholarly journals Chiral Alkyl Amine Synthesis via Catalytic Enantioselective Hydroalkylation of Enamides

2020 ◽  
Author(s):  
Deyun Qian ◽  
Srikrishna Bera ◽  
Xile Hu
Keyword(s):  
Natural Products ◽  
Functional Group ◽  
Building Blocks ◽  
Alkyl Halides ◽  
Enantioselective Synthesis ◽  
Mild Conditions ◽  
Drug Molecules ◽  
Alkyl Amines ◽  
Wide Range ◽  
Synthetic Intermediates

Chiral alkyl amines are omnipresent as bio-active molecules and synthetic intermediates. Catalytic and enantioselective synthesis of alkyl amines from readily accessible precursors is challenging. Here we develop a nickel-catalyzed hydroalkylation method to assemble a wide range of chiral alkyl amines from enamides and alkyl halides in high regio- and enantioselectivity. The method works for both non-activated and activated alkyl halides, and is able to produce enantiomerically enriched amines with two minimally differentiated alpha-alkyl substituents. The mild conditions lead to high functional group tolerance, which is demonstrated in the post-product functionalization of many natural products and drug molecules, as well as the synthesis of chiral building blocks and key intermediates to bio-active compounds.

scholarly journals Chiral Alkyl Amine Synthesis via Catalytic Enantioselective Hydroalkylation of Enamides

2020 ◽  
Author(s):  
Deyun Qian ◽  
Srikrishna Bera ◽  
Xile Hu
Keyword(s):  
Natural Products ◽  
Functional Group ◽  
Building Blocks ◽  
Alkyl Halides ◽  
Enantioselective Synthesis ◽  
Mild Conditions ◽  
Drug Molecules ◽  
Alkyl Amines ◽  
Wide Range ◽  
Synthetic Intermediates

Chiral alkyl amines are omnipresent as bio-active molecules and synthetic intermediates. Catalytic and enantioselective synthesis of alkyl amines from readily accessible precursors is challenging. Here we develop a nickel-catalyzed hydroalkylation method to assemble a wide range of chiral alkyl amines from enamides and alkyl halides in high regio- and enantioselectivity. The method works for both non-activated and activated alkyl halides, and is able to produce enantiomerically enriched amines with two minimally differentiated alpha-alkyl substituents. The mild conditions lead to high functional group tolerance, which is demonstrated in the post-product functionalization of many natural products and drug molecules, as well as the synthesis of chiral building blocks and key intermediates to bio-active compounds.

scholarly journals Modern Synthetic Strategies with Organoselenium Reagents: A Focus on Vinyl Selenones

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3148
Author(s):  
Martina Palomba ◽  
Italo Franco Coelho Dias ◽  
Ornelio Rosati ◽  
Francesca Marini
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Multiple Bond ◽  
Building Blocks ◽  
One Pot ◽  
Bond Forming ◽  
One Pot Synthesis ◽  
Bond Forming Reactions ◽  
Synthetic Transformations

In recent years, vinyl selenones were rediscovered as useful building blocks for new synthetic transformations. This review will highlight these advances in the field of multiple-bond-forming reactions, one-pot synthesis of carbo- and heterocycles, enantioselective construction of densely functionalized molecules, and total synthesis of natural products.

Recent advances in the synthesis of organic chloramines and their insights into health care

2021 ◽  
Author(s):  
G. Grace Victoria ◽  
Sabbasani Rajasekhara Reddy
Keyword(s):  
Health Care ◽  
Natural Products ◽  
Organic Nitrogen ◽  
Recent Advances ◽  
Analytical Reagents ◽  
Synthetic Intermediates ◽  
Organic Chloramines

Organic nitrogen–chlorine compounds and their derivatives are important heterocyclic motifs, exhibiting applications such as N-chlorinating agents, analytical reagents, disinfectants, antipathogens, and as synthetic intermediates for drugs, polymers, and natural products.

scholarly journals Recent advances in the biosynthesis of unusual polyketide synthase substrates

2016 ◽  
Vol 33 (2) ◽  
pp. 150-161 ◽  
Author(s):  
Lauren Ray ◽  
Bradley S. Moore
Keyword(s):  
Natural Products ◽  
Polyketide Synthase ◽  
Building Blocks ◽  
Pharmacological Activities ◽  
Chemical Complexity ◽  
Recent Advances ◽  
Biological And Pharmacological Activities

Polyketides comprise a diverse class of natural products, with many important biological and pharmacological activities. Substrates functioning as starter units and extender units during their assembly significantly contribute to the chemical complexity exhibited by this class of natural products. This highlight provides an overview of the recent advances in understanding the diversity of these polyketide synthase (PKS) building blocks.

scholarly journals Recent advances in Cu-catalyzed C(sp3)–Si and C(sp3)–B bond formation

2020 ◽  
Vol 16 ◽  
pp. 691-737 ◽  
Author(s):  
Balaram S Takale ◽  
Ruchita R Thakore ◽  
Elham Etemadi-Davan ◽  
Bruce H Lipshutz
Keyword(s):  
Bond Formation ◽  
Cross Coupling ◽  
Building Blocks ◽  
Coupling Reactions ◽  
Bond Forming ◽  
Cross Coupling Reactions ◽  
Recent Advances ◽  
Bond Forming Reactions

Numerous reactions generating C–Si and C–B bonds are in focus owing to the importance of incorporating silicon or boron into new or existing drugs, in addition to their use as building blocks in cross-coupling reactions en route to various targets of both natural and unnatural origins. In this review, recent protocols relying on copper-catalyzed sp3 carbon–silicon and carbon–boron bond-forming reactions are discussed.

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