The Tetrahydrofuran Motif in Polyketide Marine Drugs

Fernández‐Peña, Laura; Díez-Poza, Carlos; González-Andrés, Paula; Barbero, Asunción

doi:10.3390/md20020120

Cited by 21 publications

(7 citation statements)

References 134 publications

(154 reference statements)

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“…Once the oxazadecaline 60 was obtained, similar chemical steps, but arranged in different order, provided the three natural compounds. In these syntheses, the two key steps are the amide coupling, mediated by HATU in the presence of sym -collidine, and a final selenoxide [ 2 , 3 ]-sigmatropic rearrangement with H 2 O 2 in pyridine [ 76 ], which was previously used by Zakarian and Lu [ 77 ]. Trichodermamides 40 , 41 and 44 have been obtained after 9, 12 or 13 steps, respectively, in moderate yields ( Scheme 9 ).…”

Section: Coumarin Derivatives From Marine World: Synthesis and Activi...mentioning

confidence: 99%

“…Compared with terrestrial substances, marine substances have different chemical features with sometimes better mechanisms of defense. It is very likely that, under the extreme conditions (e.g., low levels of oxygen, high pressures, absence of light) in which deep sea organisms live, they have adapted to this environment undergoing biochemical or physiological transformations to survive, providing sophisticated organic skeletons with interesting drug-like properties [ 1 , 2 ].…”

Section: Introductionmentioning

confidence: 99%

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Recent Advances in Biologically Active Coumarins from Marine Sources: Synthesis and Evaluation

2022

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Coumarin and its derivatives have significantly attracted the attention of medicinal chemists and chemical biologists due to their huge range of biological, and in particular, pharmacological properties. Interesting families of coumarins have been found from marine sources, which has accelerated the drug discovery process by inspiring innovation or even by the identification of analogues with remarkable biological properties. The purpose of this review is to showcase the most interesting marine-derived coumarins from a medicinal chemistry point of view, as well as the novel and useful synthetic routes described to date to achieve these chemical structures. The references that compose this overview were collected from PubMed, Mendeley and SciFinder.

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Section: Coumarin Derivatives From Marine World: Synthesis and Activi...mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Recent Advances in Biologically Active Coumarins from Marine Sources: Synthesis and Evaluation

2022

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“…On the other hand, the tetrahydrofuran moiety is broadly present in biologically active natural products of both terrestrial and marine organisms, and as such, it has raised the attention of communities of synthetic and medicinal chemists . Also, thiolane cycle-containing natural products, and their synthetic analogs have found therapeutic applications, been studied as antibiotics, antiviral, and anticancer agents or have been used in traditional Ayurvedic medicine to treat the metabolic syndrome …”

Section: Introductionmentioning

confidence: 99%

1,2-Silyl Shift-Induced Heterocyclization of Propargyl Silanes: Synthesis of Five-Membered Heterocycles Containing a Functionalized Olefin Side Chain

Kroņkalne,

Beļaunieks,

Ubaidullajevs

et al. 2023

J. Org. Chem.

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Propargyl silanes with a terminal alkyne moiety undergo a 1,2-silyl shift when activated with electrophiles such as H+, Br+, I+, and PhSe+. A method was developed to trap 1,3-transposed electrophilic centers with various internal O-, N-, and S-nucleophiles in a 5-exo manner. This synthetic procedure provided five-membered heterocycles containing a trisubstituted olefin side chain. The scope of the method includes access to tetrahydrofuran, γ-butyrolactone, 2-isooxazoline, pyrrolidine, and thiolane derivatives in yields ranging from 25 to 85% (23 examples in total). Reactions with TsNBr2 ensured complete (E)-selectivity of the newly formed olefins. Further functionalization of the obtained 1-trialkylsilyl-2-bromovinyl side chain was demonstrated by double-bond geometry-preserving electrophilic substitution and cross-coupling reactions that provided heterocycles with a trisubstituted vinyl moiety.

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“…Regarding tetrahydrofurans, Fernandes and coworkers recently reviewed the most iconic examples of total synthesis of 2,3,5-trisubstituted tetrahydrofuran-containing natural products [ 18 , 19 ]. We have also recently summarized the synthesis and biological properties of marine-derived tetrahydrofuran-containing compounds, focusing on the polyketide family [ 20 ].…”

Section: Introductionmentioning

confidence: 99%

The Tetrahydrofuran Motif in Marine Lipids and Terpenes

et al. 2022

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Heterocycles are particularly common moieties within marine natural products. Specifically, tetrahydrofuranyl rings are present in a variety of compounds which present complex structures and interesting biological activities. Focusing on terpenoids, a high number of tetrahydrofuran-containing metabolites have been isolated during the last decades. They show promising biological activities, making them potential leads for novel antibiotics, antikinetoplastid drugs, amoebicidal substances, or anticancer drugs. Thus, they have attracted the attention of the synthetics community and numerous approaches to their total syntheses have appeared. Here, we offer the reader an overview of marine-derived terpenoids and related compounds, their isolation, structure determination, and a special focus on their total syntheses and biological profiles.

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The Tetrahydrofuran Motif in Polyketide Marine Drugs

Cited by 21 publications

References 134 publications

Recent Advances in Biologically Active Coumarins from Marine Sources: Synthesis and Evaluation

Recent Advances in Biologically Active Coumarins from Marine Sources: Synthesis and Evaluation

1,2-Silyl Shift-Induced Heterocyclization of Propargyl Silanes: Synthesis of Five-Membered Heterocycles Containing a Functionalized Olefin Side Chain

The Tetrahydrofuran Motif in Marine Lipids and Terpenes

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