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Journal articles on the topic 'Polyoxygenated natural products'

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1

Noutsias, Dimitris, Ioanna Alexopoulou, Tamsyn Montagnon, and Georgios Vassilikogiannakis. "Using water, light, air and spirulina to access a wide variety of polyoxygenated compounds." Green Chemistry 14, no. 3 (2012): 601–4. https://doi.org/10.1039/c2gc16397g.

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A new set of completely green methods utilising air, light, water and spirulina to transform readily accessible furan substrates into a diverse range of synthetically useful polyoxygenated motifs commonly found in natural products is presented herein.
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2

Montagnon, Tamsyn, Maria Tofi, and Georgios Vassilikogiannakis. "Using Singlet Oxygen to Synthesize Polyoxygenated Natural Products from Furans." Accounts of Chemical Research 41, no. 8 (2008): 1001–11. http://dx.doi.org/10.1021/ar800023v.

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3

Gómez, Edison Díaz, Sándor Antus, Renáta Ferenczi, Barbara Rys, Anna Stankiewicz, and Helmut Duddeck. "Enantiodifferentiation by 1H and 13C NMR Spectroscopy (Dirhodium Method) – Selectivity of Oxygen Functionalities." Natural Product Communications 3, no. 3 (2008): 1934578X0800300. http://dx.doi.org/10.1177/1934578x0800300307.

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Chiral carbonyl compounds can easily be enantiodifferentiated by the dirhodium method. The rhodium atoms reveal a remarkable selectivity in binding to oxygen atoms, which is of great advantage for discriminating chiral polyoxygenated natural products. Amides are the strongest ligands followed by ketones and esters; ethers and alcohols/phenols are even less effective. This sequence is rationalized by electronic charges at the oxygen atoms, as obtained from density functional calculations.
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4

Yence, Merve, Dilgam Ahmadli, Damla Surmeli, Umut Mert Karacaoğlu, Sujit Pal, and Yunus Emre Türkmen. "Synthesis of acenaphthylene-fused heteroarenes and polyoxygenated benzo[j]fluoranthenes via a Pd-catalyzed Suzuki–Miyaura/C–H arylation cascade." Beilstein Journal of Organic Chemistry 20 (December 23, 2024): 3290–98. https://doi.org/10.3762/bjoc.20.273.

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Acenaphthylene-fused heteroarenes with a variety of five- and six-membered heterocycles such as thiophene, furan, benzofuran, pyrazole, pyridine and pyrimidine were synthesized via an efficient Pd-catalyzed reaction cascade in good to high yields (45–90%). This cascade involves an initial Suzuki–Miyaura cross-coupling reaction between 1,8-dihalonaphthalenes and heteroarylboronic acids or esters, followed by an intramolecular C–H arylation under the same conditions to yield the final heterocyclic fluoranthene analogues. The method was further employed to access polyoxygenated benzo[j]fluoranthe
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5

Galobardes, Marta, Miguel Gascon, Pedro Romea, and Felix Urpi. "A Stereoselective Aldol-Reduction Approach to Polyoxygenated Natural Products. Synthesis of C1-C6 Fragment of Erythronolides." Letters in Organic Chemistry 2, no. 4 (2005): 312–15. http://dx.doi.org/10.2174/1570178054038920.

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6

Myles, D. C., and Samuel J. Danishefsky. "The synthesis of polyoxygenated natural products via fully synthetic branched pyranose derivatives: application to the erythronolide problem." Pure and Applied Chemistry 61, no. 7 (1989): 1235–42. http://dx.doi.org/10.1351/pac198961071235.

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7

Keinan, Ehud, and Subhash C. Sinha. "Oxidative polycyclizations with rhenium(VII) oxides." Pure and Applied Chemistry 74, no. 1 (2002): 93–105. http://dx.doi.org/10.1351/pac200274010093.

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The consecutive oxidative polycyclization reaction with rhenium(VII) oxides represents a highly stereoselective synthetic tool by which polyenes that contain a bis-homoallylic alcohol can be transformed into poly-THF products in a single step. On the basis of a detailed study with model substrates, a set of rules is proposed to predict product configurations in the polycyclization reactions with trifluoroacetylperrhenate. This methodology is exceptionally useful for the synthesis of polyoxygenated carbon skeletons that contain many stereogenic centers, and for the Annonaceous acetogenins in pa
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8

Evans, David A., Andrew M. Ratz, Bret E. Huff, and George S. Sheppard. "Mild alcohol methylation procedure for the synthesis of polyoxygenated natural products. Applications to the synthesis of lonomycin A." Tetrahedron Letters 35, no. 39 (1994): 7171–72. http://dx.doi.org/10.1016/0040-4039(94)85352-5.

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9

Mohamed, Tarik A., Abdelsamed I. Elshamy, Mohamed H. Abd El-Razek, et al. "Sarcoconvolutums F and G: Polyoxygenated Cembrane-Type Diterpenoids from Sarcophyton convolutum, a Red Sea Soft Coral." Molecules 27, no. 18 (2022): 5835. http://dx.doi.org/10.3390/molecules27185835.

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Natural products and chemical analogues are widely used in drug discovery, notably in cancer and infectious disease pharmacotherapy. Sarcophyton convolutum (Alcyoniidae) a Red Sea–derived soft coral has been shown to be a rich source of macrocyclic diterpenes and cyclized derivatives. Two previously undescribed polyoxygenated cembrane-type diterpenoids, sarcoconvolutums F (1) and G (2), as well as four identified analogues (3–6) together with a furan derivate (7) were isolated from a solvent extract. Compounds were identified by spectroscopic techniques, including NMR, HREIMS, and CD, together
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10

Kouridaki, Antonia, Tamsyn Montagnon, Dimitris Kalaitzakis, and Georgios Vassilikogiannakis. "Using singlet oxygen to synthesise the CDE-ring system of the pectenotoxins." Organic & biomolecular chemistry 11, no. 4 (2012): 537–41. https://doi.org/10.1039/C2OB27158C.

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A non-classical route to the key CDE-ring fragment of the pectenotoxins has been developed which showcases a remarkable singlet oxygen-mediated cascade reaction sequence to install the complete DE ring system.
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11

EVANS, D. A., A. M. RATZ, B. E. HUFF, and G. S. SHEPPARD. "ChemInform Abstract: Mild Alcohol Methylation Procedures for the Synthesis of Polyoxygenated Natural Products. Applications to the Synthesis of Lonomycin A." ChemInform 26, no. 15 (2010): no. http://dx.doi.org/10.1002/chin.199515291.

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12

Young, Gyu Kim, Whang Konghyun, R. J. Cooke, and Jin K. Cha. "A stereoselective osmylation approach to polyoxygenated natural products. Synthesis of C(1)-C(7) and C(7)-C(13) subunits of erythronolide A." Tetrahedron Letters 31, no. 23 (1990): 3275–78. http://dx.doi.org/10.1016/s0040-4039(00)89042-5.

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13

Maeda, Gasper, Pieter J. Gilissen, Catarina Bourgard, et al. "Polyoxygenated cyclohexene derivatives and flavonoids from the leaves of Uvaria pandensis." Fitoterapia 158, no. 105170 (2021). https://doi.org/10.5281/zenodo.5819766.

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14

Kalesse, Markus, and Daniel Lücke. "Chiral Polyoxygenated Tertiary Alcohols through Kiyooka Aldol Reaction." Synlett, February 17, 2022. http://dx.doi.org/10.1055/a-1775-7590.

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AbstractHere we present our work on a Kiyooka aldol protocol for the stereoselective synthesis of tertiary alcohols. In the obtained products, three oxygenated carbon atoms that could further be differentiated flank the chiral tertiary alcohol. This methodology can be applied to simple aromatic or aliphatic aldehydes and more complex substrates bearing a chiral center in the α- and/or β-position. For complex substrates, an unexpected dependency between stereoselectivity and double-bond geometry of the ketene acetal was observed. Furthermore, applications in or towards the synthesis of natural
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15

Montagnon, Tamsyn, Maria Tofi, and Georgios Vassilikogiannakis. "ChemInform Abstract: Using Singlet Oxygen to Synthesize Polyoxygenated Natural Products from Furans." ChemInform 39, no. 48 (2008). http://dx.doi.org/10.1002/chin.200848272.

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16

Pote, Aditya R., Shayne M. Weierbach, Mark Peczuh, and Kyle M. Lambert. "Advancements in the Synthesis of Polyoxygenated Oxepanes and Thiepanes for Applications to Natural Products." Organic Chemistry Frontiers, 2024. http://dx.doi.org/10.1039/d4qo00380b.

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Oxepanes are central motifs and tenants of many biologically important molecules, and their synthetic construction often presents a challenge to chemists due to consequential entropic and enthalpic barriers that have...
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17

MYLES, D. C., and S. J. DANISHEFSKY. "ChemInform Abstract: The Synthesis of Polyoxygenated Natural Products via Fully Synthetic Branched Pyranose Derivatives: Application to the Erythronolide Problem." ChemInform 21, no. 16 (1990). http://dx.doi.org/10.1002/chin.199016365.

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18

DANISHEFSKY, S. J. "ChemInform Abstract: Reflections on Organic Synthesis: The Evolution of a General Strategy for the Stereoselective Construction of Polyoxygenated Natural Products." ChemInform 18, no. 35 (1987). http://dx.doi.org/10.1002/chin.198735377.

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