Spirocyclic Motifs in Natural Products

Chupakhin, Evgeny; Babich, Olga; Prosekov, Alexander; Asyakina, Lyudmila; Krasavin, Mikhail

doi:10.3390/molecules24224165

Cited by 157 publications

(109 citation statements)

References 116 publications

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“…This structural feature is often present in natural products isolated from different sources, from plants to marine organisms. [1] Examples of spirocompounds of natural origin include horsfiline, a natural product isolated from Horsfielda superba, [1d] βvetivone, extracted from vetiver oil, [1e] or (À )-gleenol isolated from the brown alga Taonia atomaria (Figure 1). [1f] Spirocyclic compounds have also found some interesting applications as privileged ligands for asymmetric catalysis such as spinol, [2] or in the production of circularly polarized photoluminescence.…”

mentioning

confidence: 99%

Enantioselective Synthesis of Functionalized Diazaspirocycles from 4‐Benzylideneisoxazol‐5(4H)‐one Derivatives and Isocyanoacetate Esters

et al. 2020

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Enantioenriched spirocyclic compounds bearing three contiguous stereocenters and high functionalization were obtained through a formal [3+2] cycloaddition reaction catalyzed by a cooperative system. The spiro compounds were synthesized from 4‐arylideneisoxazol‐5‐ones and isocyanoacetate esters using a bifunctional squaramide/Brønsted base organocatalyst derived from a Cinchona alkaloid and silver oxide as Lewis acid. This method afforded two out of the four possible diastereomers with good yields and high enantiomeric excess for both diastereomers.

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mentioning

confidence: 99%

Enantioselective Synthesis of Functionalized Diazaspirocycles from 4‐Benzylideneisoxazol‐5(4H)‐one Derivatives and Isocyanoacetate Esters

et al. 2020

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“…Cultures of cells, tissues, and plant organs are increasingly popular alternative sources of valuable secondary metabolites. This is due to the limited reserves of medicinal raw materials, the impossibility of growing many species using the plantation method and the difficulties in developing methods for the chemical synthesis of a number of natural compounds [ 15 , 19 ].…”

Section: Genetic Engineering and Biotechnology In The In Vitro Promentioning

confidence: 99%

“…Therefore, embryos, usually zygotic, are used as an object; the transformation of somatic embryos was tested. Callus tissue, which can also be used as an object, develops from the tissues of the flap of immature zygotic embryos on a nutrient medium [ 15 , 19 , 41 ].…”

Section: Genetic Engineering and Biotechnology In The In Vitro Promentioning

confidence: 99%

Modern Trends in the In Vitro Production and Use of Callus, Suspension Cells and Root Cultures of Medicinal Plants

et al. 2020

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This paper studies modern methods of producing and using callus, suspension cells and root cultures of medicinal plants in vitro. A new solution for natural product production is the use of an alternative source of renewable, environmentally friendly raw materials: callus, suspension and root cultures of higher plants in vitro. The possibility of using hairy root cultures as producers of various biologically active substances is studied. It is proven that the application of the genetic engineering achievements that combine in vitro tissue culture and molecular biology methods was groundbreaking in terms of the intensification of the extraction process of compounds significant for the medical industry. It is established that of all the callus processing methods, suspension and root cultures in vitro, the Agrobacterium method is the most widely used in practice. The use of agrobacteria has advantages over the biolistic method since it increases the proportion of stable transformation events, can deliver large DNA segments and does not require special ballistic devices. As a result of the research, the most effective strains of agrobacteria are identified.

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“…On the other hand, the balanced rigidity of spirocycles is high enough to reduce the entropic penalty upon binding to a protein target. [150][151][152] Initial attempts to synthesize precursors of naturally occurring spirocycles using an electrochemical key step were undertaken by the groups of Yamamura and Swenton in the late 20 th century. [153][154][155][156][157] These scientists successfully synthesized discorhabdin C (85) through anodic oxidation of bromophenol derivative 83, which was easily accessible from 3-nitro-4,5-dimethoxybenzaldehyde (81) and 3,5-dibromotyramine (82).…”

Section: Spirocyclesmentioning

confidence: 99%

Anodic Oxidation as an Enabling Tool for the Synthesis of Natural Products

Geske

Sato²,

Opatz³

2020

Synthesis

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Electrochemistry provides a valuable toolbox for organic synthesis and offers an appealing, environmentally benign alternative to the use of stoichiometric quantities of chemical oxidants or reductants. Its potential to control current efficiency along with providing alternative reaction conditions in a classical sense makes electrochemistry a suitable method for large-scale industrial transformations as well as for laboratory applications in the synthesis of complex molecular architectures. Even though research in this field has intensified over the recent decades, many synthetic chemists still hesitate to add electroorganic reactions to their standard repertoire, and hence, the full potential of preparative organic electrochemistry has not yet been unleashed. This short review highlights the versatility of anodic transformations by summarizing their application in natural product synthesis.1 Introduction2 Shono-Type Oxidation3 C–N/N–N Bond Formation4 Aryl–Alkene/Aryl–Aryl Coupling5 Cycloadditions Triggered by Oxidation of Electron-Rich Arenes6 Spirocycles7 Miscellaneous Transformations8 Future Prospects

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Spirocyclic Motifs in Natural Products

Cited by 157 publications

References 116 publications

Enantioselective Synthesis of Functionalized Diazaspirocycles from 4‐Benzylideneisoxazol‐5(4H)‐one Derivatives and Isocyanoacetate Esters

Enantioselective Synthesis of Functionalized Diazaspirocycles from 4‐Benzylideneisoxazol‐5(4H)‐one Derivatives and Isocyanoacetate Esters

Modern Trends in the In Vitro Production and Use of Callus, Suspension Cells and Root Cultures of Medicinal Plants

Anodic Oxidation as an Enabling Tool for the Synthesis of Natural Products

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