Relevant bibliographies by topics / Marine polypropionates

Academic literature on the topic 'Marine polypropionates'

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Published: 4 June 2021
Last updated: 8 February 2022

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Journal articles on the topic "Marine polypropionates"

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T. Davies-Coleman, Michael, and Mary J. Garson. "Marine polypropionates." Natural Product Reports 15, no. 5 (1998): 477. http://dx.doi.org/10.1039/a815477y.

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Davies-Coleman, Michael T., and Mary J. Garson. "ChemInform Abstract: Marine Polypropionates." ChemInform 30, no. 10 (June 17, 2010): no. http://dx.doi.org/10.1002/chin.199910319.

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Esposito, Germana, Roberta Teta, Gerardo Della Sala, Joseph Pawlik, Alfonso Mangoni, and Valeria Costantino. "Isolation of Smenopyrone, a Bis-γ-Pyrone Polypropionate from the Caribbean Sponge Smenospongia aurea." Marine Drugs 16, no. 8 (August 17, 2018): 285. http://dx.doi.org/10.3390/md16080285.

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The organic extract of the Caribbean sponge Smenospongia aurea has been shown to contain an array of novel chlorinated secondary metabolites derived from a mixed PKS-NRPS biogenetic route such as the smenamides. In this paper, we report the presence of a biogenetically different compound known as smenopyrone, which is a polypropionate containing two γ-pyrone rings. The structure of smenopyrone including its relative and absolute stereochemistry was determined by spectroscopic analysis (NMR, MS, ECD) and supported by a comparison with model compounds from research studies. Pyrone polypropionates are unprecedented in marine sponges but are commonly found in marine mollusks where their biosynthesis by symbiotic bacteria has been hypothesized and at least in one case demonstrated. Since pyrones have recently been recognized as bacterial signaling molecules, we speculate that smenopyrone could mediate inter-kingdom chemical communication between S. aurea and its symbiotic bacteria.
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Bromley, Candice L., Wendy L. Popplewell, Shirley C. Pinchuck, Alan N. Hodgson, and Michael T. Davies-Coleman. "Polypropionates from the South African Marine Mollusk Siphonaria oculus." Journal of Natural Products 75, no. 3 (January 27, 2012): 497–501. http://dx.doi.org/10.1021/np2009384.

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Singh, Keisham S. "Pyrone-derived Marine Natural Products: A Review on Isolation, Bio-activities and Synthesis." Current Organic Chemistry 24, no. 4 (May 9, 2020): 354–401. http://dx.doi.org/10.2174/1385272824666200217101400.

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Marine natural products (MNPs) containing pyrone rings have been isolated from numerous marine organisms, and also produced by marine fungi and bacteria, particularly, actinomycetes. They constitute a versatile structure unit of bioactive natural products that exhibit various biological activities such as antibiotic, antifungal, cytotoxic, neurotoxic, phytotoxic and anti-tyrosinase. The two structure isomers of pyrone ring are γ- pyrone and α-pyrone. In terms of chemical motif, γ-pyrone is the vinologous form of α- pyrone which possesses a lactone ring. Actinomycete bacteria are responsible for the production of several α-pyrone compounds such as elijopyrones A-D, salinipyrones and violapyrones etc. to name a few. A class of pyrone metabolites, polypropionates which have fascinating carbon skeleton, is primarily produced by marine molluscs. Interestingly, some of the pyrone polytketides which are found in cone snails are actually synthesized by actinomycete bacteria. Several pyrone derivatives have been obtained from marine fungi such as Aspergillums flavus, Altenaria sp., etc. The γ-pyrone derivative namely, kojic acid obtained from Aspergillus fungus has high commercial demand and finds various applications. Kojic acid and its derivative displayed inhibition of tyrosinase activity and, it is also extensively used as a ligand in coordination chemistry. Owing to their commercial and biological significance, the synthesis of pyrone containing compounds has been given attention over the past years. Few reviews on the total synthesis of pyrone containing natural products namely, polypropionate metabolites have been reported. However, these reviews skipped other marine pyrone metabolites and also omitted discussion on isolation and detailed biological activities. This review presents a brief account of the isolation of marine metabolites containing a pyrone ring and their reported bio-activities. Further, the review covers the synthesis of marine pyrone metabolites such as cyercene-A, placidenes, onchitriol-I, onchitriol-II, crispatene, photodeoxytrichidione, (-) membrenone-C, lihualide-B, macrocyclic enol ethers and auripyrones-A & B.
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Sabitha, Gowravaram, Peddabuddi Gopal, and Jhillu S. Yadav. "Total synthesis of the marine polypropionates, siphonarienal, siphonarienone, and pectinatone." Tetrahedron: Asymmetry 20, no. 19 (October 2009): 2205–10. http://dx.doi.org/10.1016/j.tetasy.2009.08.021.

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Beukes, Denzil R., and Michael T. Davies-Coleman. "Novel polypropionates from the South African marine mollusc Siphonaria capensis." Tetrahedron 55, no. 13 (March 1999): 4051–56. http://dx.doi.org/10.1016/s0040-4020(99)00093-9.

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Sato, Seizo, Fumie Iwata, Takako Mukai, Shoichi Yamada, Jiro Takeo, Akihisa Abe, and Hiroyuki Kawahara. "Indoxamycins A−F. Cytotoxic Tricycklic Polypropionates from a Marine-Derived Actinomycete." Journal of Organic Chemistry 74, no. 15 (August 7, 2009): 5502–9. http://dx.doi.org/10.1021/jo900667j.

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Carbone, Marianna, M. Letizia Ciavatta, Jian-Rong Wang, Ilaria Cirillo, Véronique Mathieu, Robert Kiss, Ernesto Mollo, Yue-Wei Guo, and Margherita Gavagnin. "Extending the Record of Bis-γ-pyrone Polypropionates from Marine Pulmonate Mollusks." Journal of Natural Products 76, no. 11 (November 2013): 2065–73. http://dx.doi.org/10.1021/np400483c.

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Ziegler, Frederick E., and Michael R. Becker. "Total synthesis of (-)-denticulatins A and B: marine polypropionates from Siphonaria denticulata." Journal of Organic Chemistry 55, no. 9 (April 1990): 2800–2805. http://dx.doi.org/10.1021/jo00296a044.

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Dissertations / Theses on the topic "Marine polypropionates"

1

Franklin, A. S. "Studies towards the total synthesis of marine derived polypropionates." Thesis, University of Cambridge, 1995. https://www.repository.cam.ac.uk/handle/1810/272999.

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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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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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4

Lister, Troy, and mike perkins@flinders edu au. "Total Synthesis of Auripyrone A and Related Metabolites." Flinders University. School of Chemistry, Physics and Earth Sciences, 2006. http://catalogue.flinders.edu.au./local/adt/public/adt-SFU20060804.125858.

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In recent decades the emergence of marine polypropionate natural products as compounds of diverse structural complexity and intriguing biological activity has influenced the advancement of asymmetric synthesis and predicated detailed studies of marine ecology. The introductory chapter of this thesis explores the nature of marine natural products, including their structure, biological activity and biosynthesis. Additionally, a brief review of the aldol reaction is presented. This well established biomimetic chemical transformation underpins polyketide synthesis and was utilised extensively in the research contributing to this dissertation. Chapter Two describes the first asymmetric total synthesis of the two marine polypropionates isolated from specimens of Siphonaria australis by Hochlowski et al. in 1984. Spectroscopic analysis revealed hemiacetal 22 and ester 23 to be identical to the secondary metabolites extracted from the marine pulmonate. The synthetic approach to hemiacetal 22 utilised lactate derived ketone (S)-67 to control the configuration of the C7 and C8 stereocentres and involved the discovery of a mild protocol for the synthesis of trimethylsilyl enol ether 109, which was employed for a Mukaiyama aldol homologation reaction. Additionally, ester 23 was synthesised from hemiacetal 22 via a retro-Claisen fragmentation. The retro-Claisen approach utilised in the synthesis of ester 23 was extended in Chapter Three to serve as the pivotal transformation in an attempted total synthesis of the unusual marine polypropionate dolabriferol (30). The strategy toward dolabriferol (30) involved an iterative homologation of chiral ketone (S)-67 to install all but one of the requisite stereocentres in the natural product. Chemoselective deprotection of acyclic precursor 160 gave the elaborate 2,4,6-trioxaadamantane 167, whose participation as a protecting group mimic lead to the formation of ester 169 after reaction of the polycycle 167 with base. The synthesis of ester 169, which represents a direct precursor to dolabriferol (30), was achieved in 16 steps with an overall yield of 24%. Unfortunately, a robust protecting group on ester 169 prohibited a synthesis of dolabriferol (30), but intriguingly in one deprotection of ester 169 with aqueous hydrofluoric acid, spiroacetal 172 was isolated. Chapter Four describes the first total synthesis of cytotoxic marine polypropionate auripyrone A (78) and establishes the absolute configuration of this important natural product as that depicted for compound 78. The requisite C8-C12 stereopentad of auripyrone A (78) was formulated from Evans� dipropionate equivalent 53 in a double stereodifferentiating aldol reaction, followed by syn-reduction to give diol 206. Differentiation of the secondary alcohols in compound 206 was achieved by migration of the PMB protecting group and protection at C11 with the requisite acyloxy group of auripyrone A (78). Differential protection was critical to achieving selective spiroacetalisation to afford the unique spiroacetal dihydropyrone core of the natural product. The utility of LiHMDS for highly selective double stereodifferentiating aldol homologations of sensitive fragments is also discussed. This mild aldol protocol was pivotal to forming the carbogenic skeleton of auripyrone A, in particular, elaborate adduct 278.
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