Relevant bibliographies by topics / Tridachiahydropyrone

Academic literature on the topic 'Tridachiahydropyrone'

Author: Grafiati
Published: 4 June 2021
Last updated: 3 February 2022

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Journal articles on the topic "Tridachiahydropyrone"

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Jeffery, David W., Michael V. Perkins, and Jonathan M. White. "Synthesis of the Putative Structure of Tridachiahydropyrone." Organic Letters 7, no. 8 (April 2005): 1581–84. http://dx.doi.org/10.1021/ol050236d.

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Sharma, Pallavi, Nicholas Griffiths, and John E. Moses. "Biomimetic Synthesis and Structural Revision of (±)-Tridachiahydropyrone." Organic Letters 10, no. 18 (September 18, 2008): 4025–27. http://dx.doi.org/10.1021/ol8015836.

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Jeffery, David W., Michael V. Perkins, and Jonathan M. White. "Synthesis of an Analogue of the Marine Polypropionate Tridachiahydropyrone." Organic Letters 7, no. 3 (February 2005): 407–9. http://dx.doi.org/10.1021/ol0478178.

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Moses, John, and Pallavi Sharma. "Photochemical Studies of the Tridachiahydropyrones in Seawater." Synlett 2010, no. 04 (December 2, 2009): 525–28. http://dx.doi.org/10.1055/s-0029-1218544.

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Sharma, Pallavi, Barry Lygo, William Lewis, and John E. Moses. "Biomimetic Synthesis and Structural Reassignment of the Tridachiahydropyrones." Journal of the American Chemical Society 131, no. 16 (April 29, 2009): 5966–72. http://dx.doi.org/10.1021/ja900369z.

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Sharma, Pallavi, Nicholas Griffiths, and John E. Moses. "ChemInform Abstract: Biomimetic Synthesis and Structural Revision of (.+-.)-Tridachiahydropyrone." ChemInform 40, no. 4 (January 27, 2009). http://dx.doi.org/10.1002/chin.200904176.

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7

Jeffery, David W., Michael V. Perkins, and Jonathan M. White. "Synthesis of an Analogue (I) of the Marine Polypropionate Tridachiahydropyrone (II)." ChemInform 36, no. 25 (June 21, 2005). http://dx.doi.org/10.1002/chin.200525206.

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Dissertations / Theses on the topic "Tridachiahydropyrone"

1

Jeffery, David William, and david jeffery@awri com au. "Total Synthesis of the Putative Structure of Tridachiahydropyrone." Flinders University. Chemistry, Physics and Earth Science, 2005. http://catalogue.flinders.edu.au./local/adt/public/adt-SFU20050603.095257.

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Polypropionate marine natural products have emerged as a class of compounds that display a high degree of structural diversity. Specifically, metabolites such as that reported as tridachiahydropyrone (7), isolated from sacoglossan molluscs, display novel ring systems. The introductory chapter gives some background on tridachione marine natural products and outlines the isolation of metabolites from several species of sacoglossan mollusc. Chapter One also gives examples of the utility of the tandem conjugate addition-Dieckmann condensation approach being applied to the synthesis of these compounds. Chapter Two describes the development of the tandem conjugate addition-Dieckmann condensation and subsequent trans methylation approach to cyclohexenone rings. The synthetic strategy utilised chiral, functionalised cyclohexenone rings as synthons in the formation of bicyclic ring systems, so development of the carbocyclic ring formation was of vital importance to the overall strategy. Examples are given which confirm the viability of the proposed synthetic route to cyclohexenones such as 91, 92 and 104 from the reaction of [alpha,beta]-unsaturated carbonyl compounds 39 and 59 with dialkyl and dialkenyl Gilman cuprates. Chapter Three describes the incorporation of chiral cyclohexenone 117 into the bicyclic framework of model compound 105, analogous to the marine natural product reported as tridachiahydropyrone (7). The chapter explores the use of cyclohexenone precursor 43 that contained the total carbon framework of the bicyclic core of the desired pyrone. Once again, a tandem conjugate addition-cyclisation reaction was employed using a dialkyl Gilman cuprate, followed by trans methylation to give the requisite cyclohexenone synthon 117. A novel Eaton’s reagent-promoted intramolecular cyclisation of acid 122 to pyrone 123 was then effected. Subsequent O-methylation afforded [alpha]-methoxy-[beta]-methyl-[gamma]-pyrone 105 as a single enantiomer, which had the identical core structure to the natural product. The structure, including relative stereochemistry of 105, was confirmed by single crystal X-ray analysis. Chapter Four builds on the previous two chapters and describes the conjugate addition-cyclisation with a higher order Gilman cuprate derived from vinyl bromide 44, which would deliver the vinyl side-chain required for the synthesis of reported natural product 7. The same acyclic precursor 43 as used in Chapter Three was cyclised and methylated to yield yet another cyclohexenone synthon 41. A single crystal X-ray analysis of related alcohol 162 confirmed the relative stereochemistry and structure. Another novel P2O5-mediated intramolecular cyclisation was achieved to give pyrone 168 and O-methylation provided a compound with the reported structure of natural product 7 as a single enantiomer. The structure of synthetic 7 was established unequivocally through extensive NMR studies. Comparisons of spectral data confirmed that natural tridachiahydropyrone was not the same as synthetic compound 7, so revision of the assigned natural product structure is warranted. Several other analogues were also synthesised using this methodology, highlighting the versatility of the method under development.
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2

Powell, Kimberley Jade. "Synthetic and biophysical studies on the tridachiahydropyrone family of natural products." Thesis, University of Nottingham, 2014. http://eprints.nottingham.ac.uk/14228/.

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This thesis primarily details synthetic and biophysical studies on the tridachiahydropyrone family of natural products. The general aim of this work was to explore an hypothesis regarding the location and function of these metabolites, isolated from sacoglossan molluscs. Specifically, it was hypothesised that tridachiahydropyrone is synthesised photochemically from linear polyene precursors via a selective double bond isomerisation-6pi electrocyclisation sequence which occurs within the cell membrane of the producing organism. Furthermore, it was postulated that this reaction sequence, and subsequent photochemical transformations of tridachiahydropyrone into the related products phototridachiahydropyrone and oxytridachiahydropyrone, serve to protect the producing mollusc from the damaging effects of UV radiation. Firstly, the proposed polyene precursors were synthesised using a convergent strategy dependent upon a late-stage Suzuki coupling. Their photochemical, biomimetic conversion into tridachiahydropyrone, phototridachiahydropyrone and oxytridachiahydropyrone, was then accomplished. The interactions of tridachiahydropyrone and its biomimetic precursors with model membrane systems were next explored, using a fluorescence spectroscopic technique. This work demonstrated that the molecules bind to phospholipid vesicles (PLVs) of varying compositions. The synthesis of tridachiahydropyrone within the PLVs was also achieved The propensity of the compounds to act as sunscreens was lastly investigated, by measuring the degree of protection against photochemically-induced lipid peroxidation they conferred on irradiated PLVs, using the thiobarbituric acid reactive substances assay. At high compound concentrations the compounds were found to act as sunscreens, whilst at lower concentrations pro-oxidant activity was observed. In addition to this main work, methodology for the palladium-catalysed cyanation of vinyl halides with acetone cyanohydrin was developed. Conditions were optimised using beta-bromostyrene, and shown to be applicable to a range of diverse substrates. The protocol proved chemoselective for vinyl bromides in the presence of aryl bromides, which were left unaffected and available for further chemical transformations, adding to the synthetic utility of the reaction.
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3

Kasprzyk, Milena, and milena kasprzyk@freehills com. "Synthetic Studies Towards the Tridachione Family of Marine Natural Products." Flinders University. Chemistry, Physics and Earth Sciences, 2008. http://catalogue.flinders.edu.au./local/adt/public/adt-SFU20081107.085933.

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Since the middle of the 20th century, significant interest has evolved from the scientific community towards the polypropionate family of marine natural products. A number of these compounds have been shown to possess significant biological activity, and this property, as well as their structural complexity, has driven numerous efforts towards their synthesis. The first chapter provides an introduction into the world of polypropionates, with a discussion on synthetic studies into a number of members of the tridachiapyrone family. Fundamental synthetic concepts utilised in this thesis towards the preparation of polyketides are also described, with a focus on their application towards the synthesis of 9,10-deoxytridachione, anti tridachiahydropyrone and syn tridachiahydropyrone. Chapter 2 describes the work undertaken towards the total synthesis of 9,10-deoxytridachione. The novel tandem conjugate addition-Dieckmann condensation of complex enones developed previously in the Perkins group was used to generate anti methylated cyclohexenones as key synthetic intermediates. The conversion of the cyclohexenones into the corresponding cyclohexadienes via allylic alcohols was attempted, utilising a Grignard-mediated reaction to achieve the selective 1,2-reduction. Studies into the Grignard-mediated reduction were also undertaken on seven additional cyclohexenones, in order to investigate the utility and scope of the reaction. The extension of the methodology previously developed for the synthesis of cyclohexenones is the subject of Chapter 3. This section describes investigations into the synthesis of stereochemically-diverse cyclohexenones from complex enones. The conjugate addition-Dieckmann condensation strategy was extended successfully towards the synthesis of a syn methylated cyclohexenone, which allowed the synthesis of the proposed true structure of tridachiahydropyrone to be pursued. The methodology developed in Chapter 3 was utilised in Chapter 4 to synthesise a model system of syn tridachiahydropyrone. A comparative analysis of the NMR data of the syn model, an anti model and anti tridachiahydropyrone with the natural product indicated that the true structure of tridachiahydropyrone may indeed have syn stereochemistry. The synthesis of syn tridachiahydropyrone was attempted, and to this end a suitable cyclohexanone was successfully synthesised. However, the subsequent methylation-elimination cascade failed to furnish the desired syn methylated cyclohexenone, producing only an anti methylated cyclohexanone. The stereochemistry of the methylation was deduced using high and low variable temperature NMR coupled with selective irradiation NOESY.
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Books on the topic "Tridachiahydropyrone"

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Powell, Kimberley Jade. Synthetic and Biophysical Studies on the Tridachiahydropyrone Family of Natural Products. Cham: Springer International Publishing, 2016. http://dx.doi.org/10.1007/978-3-319-22069-7.

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2

Powell, Kimberley Jade. Synthetic and Biophysical Studies on the Tridachiahydropyrone Family of Natural Products. Springer, 2016.

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3

Powell, Kimberley Jade. Synthetic and Biophysical Studies on the Tridachiahydropyrone Family of Natural Products. Springer, 2015.

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Book chapters on the topic "Tridachiahydropyrone"

1

Powell, Kimberley Jade. "Synthesis of the Tridachiahydropyrones and their Biomimetic Precursors." In Springer Theses, 25–38. Cham: Springer International Publishing, 2015. http://dx.doi.org/10.1007/978-3-319-22069-7_2.

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2

Powell, Kimberley Jade. "Interactions of the Tridachiahydropyrones with Model Membrane Systems: Biophysical Studies." In Springer Theses, 39–58. Cham: Springer International Publishing, 2015. http://dx.doi.org/10.1007/978-3-319-22069-7_3.

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3

Powell, Kimberley Jade. "Investigations into the Photoprotective and Antioxidant Properties of the Tridachiahydropyrones." In Springer Theses, 59–72. Cham: Springer International Publishing, 2015. http://dx.doi.org/10.1007/978-3-319-22069-7_4.

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