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Relevant bibliographies by topics / Tetracyclic diterpenes

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Academic literature on the topic 'Tetracyclic diterpenes'

Author: Grafiati

Published: 22 February 2023

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Journal articles on the topic "Tetracyclic diterpenes"

1

Shen, Yong, Wen-Juan Liang, Ya-Na Shi, Edward J. Kennelly, and Da-Ke Zhao. "Structural diversity, bioactivities, and biosynthesis of natural diterpenoid alkaloids." Natural Product Reports 37, no. 6 (2020): 763–96. http://dx.doi.org/10.1039/d0np00002g.

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2

Chen, Yan-Ni, Xiao Ding, Dong-Mei Li, Mao Sun, Lei Yang, Yu Zhang, Ying-Tong Di, Xin Fang, and Xiao-Jiang Hao. "Diterpenoids with an unprecedented ring system from Euphorbia peplus and their activities in the lysosomal-autophagy pathway." Organic & Biomolecular Chemistry 19, no. 7 (2021): 1541–45. http://dx.doi.org/10.1039/d0ob02414g.

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3

Marcos, Isidro S., Rosalina F. Moro, Santiago Carballares M., and Julio G. Urones. "Cyclization of Bicyclic Diterpenes Promoted by SmI2. Synthesis of Tri- and Tetracyclic Diterpenes." Synlett 2002, no. 03 (2002): 0458–62. http://dx.doi.org/10.1055/s-2002-20465.

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4

Vasas, Andrea, Judit Hohmann, Peter Forgo, and Pál Szabó. "New tri- and tetracyclic diterpenes from Euphorbia villosa." Tetrahedron 60, no. 23 (May 2004): 5025–30. http://dx.doi.org/10.1016/j.tet.2004.04.028.

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5

Marcos, I. S., M. A. Cubillo, R. F. Moro, S. Carballares, D. Díez, P. Basabe, C. F. Llamazares, et al. "Synthesis of tri- and tetracyclic diterpenes. Cyclisations promoted by SmI2." Tetrahedron 61, no. 4 (January 2005): 977–1003. http://dx.doi.org/10.1016/j.tet.2004.09.116.

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6

GOLDSMITH, D. "ChemInform Abstract: The Total Synthesis of Tri- and Tetracyclic Diterpenes." ChemInform 23, no. 47 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199247301.

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7

Chen, De-Lin, Feng-Peng Wang, and Xiao-Yu Liu. "A convergent approach to the tetracyclic core of atisane diterpenes." Chinese Chemical Letters 27, no. 1 (January 2016): 59–62. http://dx.doi.org/10.1016/j.cclet.2015.09.005.

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8

Adelin, Emilie, Claudine Servy, Marie-Thérèse Martin, Guillaume Arcile, Bogdan I. Iorga, Pascal Retailleau, Mercedes Bonfill, and Jamal Ouazzani. "Bicyclic and tetracyclic diterpenes from a Trichoderma symbiont of Taxus baccata." Phytochemistry 97 (January 2014): 55–61. http://dx.doi.org/10.1016/j.phytochem.2013.10.016.

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9

Smyrniotopoulos, Vangelis, Constantinos Vagias, Mukhlesur M Rahman, Simon Gibbons, and Vassilios Roussis. "Ioniols I and II, Tetracyclic Diterpenes with Antibacterial Activity, fromSphaerococcus coronopifolius." Chemistry & Biodiversity 7, no. 3 (March 2010): 666–76. http://dx.doi.org/10.1002/cbdv.200900026.

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10

Hayashi, Toshimitsu, Tomohiko Asai, and Ushio Sankawa. "Mevalonate-independent biosynthesis of bicyclic and tetracyclic diterpenes of Scoparia dulcis L." Tetrahedron Letters 40, no. 47 (November 1999): 8239–43. http://dx.doi.org/10.1016/s0040-4039(99)01748-7.

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Dissertations / Theses on the topic "Tetracyclic diterpenes"

1

BARTOLI, GABRIELE. "Synthesis of bicyclo[3.2.1]octane tetracyclic diterpenes." Doctoral thesis, 2014. http://hdl.handle.net/11573/917017.

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2

TROMBETTA, ANDREA. "Studies for the synthesis of (+)-oryzalexin S." Doctoral thesis, 2014. http://hdl.handle.net/11573/877079.

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(+) - Orizalessina S è una fitoalessina stemaranica prodotta da Oryza sativa L., la pianta del riso, in risposta agli attacchi da parte di agenti patogeni come il fungo Pyricularia oryzae Cav. o se esposta alla radiazione UV o ai metalli pesanti. E' stata isolata nel 1992 da Kodama e collaboratori. Per le sue proprietà antifungine, per la bassa abbondanza naturale e complessa struttura , in cui sono presenti due atomi di carbonio quaternari contigui e sette centri stereogenici, fanno di questo composto un obiettivo sintetico particolarmente interessante. Così, come parte della nostra ricerca sui diterpeni tetraciclici contenenti un sistema biciclo [3.2.1] ottanico, con particolare attenzione allo stato attuale ai diterpeni stemaranici, descriviamo la nostra preparazione entio e diastereoselettiva dell'intermedio trans-octaidronaftalenico, un intermedio chiave per la sintesi di (+) - oryzalexin S.
(+)-oryzalexin S is a stemarane phytoalexin produced from Oryza Sativa L., the plant of rice, in response to the attacks by patogen agents like the fungus Pyricularia oryzae Cav. or if exposed at UV radiation or heavy metals. It was isolated in 1992 by Kodama and coworkers. Its antifungal properties, low natural abundance and complex structure, in which two contiguous quaternary carbons and seven stereogenic centers are present, make this compound a particularly interesting synthetic target. Thus, as a part of our research on tetracyclic diterpenes containing a bicyclo[3.2.1]octane system, focusing at present on stemarane diterpenes2,3, we wish now to describe our recently accomplished enantio and diastereoselective preparation of key trans-octahydronaphthalenic intermediate for the synthesis of (+)-oryzalexin S .

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Books on the topic "Tetracyclic diterpenes"

1

Barton, D. H. R., J. R. Hanson, and R. A. Raphael. Tetracyclic Diterpenes. Elsevier Science & Technology Books, 2013.

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Book chapters on the topic "Tetracyclic diterpenes"

1

Goldsmith, David. "The Total Synthesis of Tri- and Tetracyclic Diterpenes." In Total Synthesis of Natural Products, 1–243. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2007. http://dx.doi.org/10.1002/9780470129715.ch1.

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2

Taber, Douglass F. "Intramolecular Diels-Alder Cycloaddition: 7-Isocyanoamphilecta- 11(20),15-diene (Miyaoka), (–)-Scabronine G (Kanoh), Basiliolide B (Stoltz), Hirsutellone B (Uchiro), Echinopine A (Chen)." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0078.

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The amphilectane diterpenes, exemplified by 7-isocyanoamphilecta-11(20),15-diene 3, have been little investigated. In the course of a synthesis of 3, Hiroaki Miyaoka of the Tokyo University of Pharmacy and Life Sciences took advantage (Synlett 2011, 547) of the kinetic enolization and silylation of 1 to convert it into a trienone that spontaneously cyclized to 2. Scabronine G 6, isolated from the mushroom Sarcodon scabrosus, was found to enhance the secretion of neurotrophic factors from 1321N1 astrocytoma cells. To set the absolute configuration of the two quaternary centers that are 1, 4 on the cyclohexane ring of 6, Naoki Kanoh and Yoshiharu Iwabuchi of Tohoku University cyclized (Org. Lett. 2011, 13, 2864) 4 to 5. Although described by the authors as a double Michael addition, this transformation has the same connectivity as an intramolecular Diels-Alder cycloaddition. The diterpenes isolated from the genus Thapsia, represented by basiliolide B 9, induce rapid mobilization of intracellular Ca2+ stores. Brian M. Stoltz of Caltech effected (Angew. Chem. Int. Ed. 2011, 50, 3688) Claisen rearrangement of 7 to give an intermediate that cyclized to 8 as a mixture of diastereomers. A significant challenge in the synthesis was the assembly of the delicate enol ether/lactone of 9. Hirsutellone B 12, isolated from Hirsutella nivea, shows significant antituberculosis activity. Hiromi Uchiro of the Tokyo University of Science found it useful (Org. Lett. 2011, 13, 6268) to protect the intermediate unsaturated keto ester by intermolecular cycloaddition with pentamethylcyclopentadiene before constructing the triene of 10. Simple thermolysis reversed the intermolecular addition, opening the way to intramolecular cycloaddition to give 11. The tetracyclic ring system of the diterpene echinopine A 15 represents a substantial synthetic challenge. David Y.-K. Chen of Seoul National University approached this problem (Org. Lett. 2011, 13, 5724) by Pd-mediated cyclization of 13 to the diene, which then underwent intramolecular Diels-Alder cycloaddition to give 14, with control of the relative configuration of two of the three ternary centers of 15. Double bond migration followed by oxidative cleavage of the resulting cyclohexenone then set the stage for the intramolecular cyclopropanation that completed the synthesis of 15.

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3

"Isoprenoids/Terpenes." In Natural Product Biosynthesis, 192–263. The Royal Society of Chemistry, 2022. http://dx.doi.org/10.1039/bk9781839165641-00192.

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This largest class of natural products, with >75 000 known structures, arises from a pair of five-carbon isopentenyl diphosphate isomers, one acting as a π-electron double bond carbon nucleophile, the other as an allylic cation electrophile in C–C bond alkylations. Isoprene/terpene chain growth thus occurs five carbons at a time in head-to-tail couplings by prenyl transferase enzymes. At both the C15 or C20 chain length stages, enzymes can carry out related head-to-head chain couplings to generate the C30 hexaene squalene or the C40 nonaene phytoene. Squalene is the precursor to cyclase-mediated conversion to tetracyclic sterol frameworks and pentacyclic plant systems, such as amyrin and cycloartenol. The C10 (geranyl-PP = monoterpene), C15 (farnesyl-PP = sesquiterpene), and C20 (geranylgeranyl = diterpene) head-to-tail coupled metabolites can undergo many variations of internal carbocation-mediated cyclizations to generate a large array of mono- to tetracyclic olefins and alcohols. The predominant animal sterol is the C27 membrane lipid cholesterol, available from the initial C30 biosynthetic tetracyclic lanosterol by oxygenative removal of three C–CH3 groups. This phase of sterol metabolism marks a shift from carbocation-based reactions, to radical chemistry by oxygenases, as nine O2 molecules are consumed. In further conversion of cholesterol to the female sex hormone estradiol, another eight O2 molecules are consumed, for a total of 17 O2 being reductively split in the metabolic traverse from lanosterol to cholesterol. Meroterpenoid assembly involves the intersection of isoprene biosynthetic machinery with polyketide- or indole-processing enzymes.

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4

Taber, Douglass F. "The Njardarson Synthesis of Vinigrol." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0086.

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The diterpene vinigrol 3, isolated from Virgaria nigra F-5408, is a tumor necrosis factor (TNF) inhibitor. Jon T. Njardarson of the University of Arizona envisioned (Angew. Chem. Int. Ed. 2013, 52, 8648) that Wharton fragmentation of 1 could deliver 2, suitably functionalized for elaboration to 3. The tetracyclic 1 was prepared by the triply-convergent assembly of the phenol 11. Addition of allyl magnesium bromide to 4 proceeded with high regio- and geometric selectivity, to give an alcohol that was methylated, then iodinated with inversion to give 5. Condensation of the phosphonate 7 with the derived aldehyde 6 led to the alcohol 8, that was coupled under Mitsunobu conditions with the phenol 9 to give 10. Oxidation of 11 gave an intermediate that underwent intramolecular Diels–Alder cycloaddition to deliver 12. On exposure to the Pd catalyst, 12 cyclized to the diene 13. On exposure to tBuOK/ tBuOH, the mesylate 1 smoothly fragmented to the hoped-for ketone 2. Although this has been referred to as a Grob fragmentation, in fact this reaction was developed (J. Org. Chem. 1961, 26, 4781) by Peter S. Wharton, then at the University of Wisconsin, and would more properly bear his name. Subsequent transformations took advantage of the hindered nature of the trisubstituted alkene of 2. Hydrogenation of the disubstituted alkene proceeded selectively, to give an intermediate that was condensed with 14, leading to the enone 15. Two more selective hydrogenations, with the Wittig methylenation in between, completed the construction of the pendant isopropyl group. Once the isopropyl group was installed, what remained was the oxidation of 16 to 19. The epoxidation of 17 proceeded with high facial selectivity, to give an intermediate that was carried on by iodination and reduction to the alcohol 18. Allylic oxidation converted 18 into 19, that was deprotected to give Vinigrol 3. It is instructive to compare and contrast this approach to vinigrol 3 with the two that we have previously highlighted (OHL September 6, 2010; December 24, 2012). Each strategy offers its own advantages.

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