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Relevant bibliographies by topics / Taxane synthesis][Synthesis of taxanes

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Academic literature on the topic 'Taxane synthesis][Synthesis of taxanes'

Author: Grafiati

Published: 4 June 2021

Last updated: 16 February 2022

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Journal articles on the topic "Taxane synthesis][Synthesis of taxanes"

1

Wender, Paul A., Neil F. Badham, Simon P. Conway, Paul E. Floreancig, Timothy E. Glass, Christian Gränicher, Jonathan B. Houze, et al. "The Pinene Path to Taxanes. 5. Stereocontrolled Synthesis of a Versatile Taxane Precursor." Journal of the American Chemical Society 119, no. 11 (March 1997): 2755–56. http://dx.doi.org/10.1021/ja9635387.

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Verschraegen, C. F., M. Royce, S. J. Lee, S. Movva, L. Susan, and G. Michael. "Vitamins B6 and B12 supplementation to prevent chemotherapy-induced neuropathy (CiN): Interim analysis of the taxane cohort." Journal of Clinical Oncology 27, no. 15_suppl (May 20, 2009): e20621-e20621. http://dx.doi.org/10.1200/jco.2009.27.15_suppl.e20621.

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e20621 Background: Chemotherapy-induced neuropathy (CiN) is common with heavy metals, taxanes, and vinca alcaloids. Pyridoxine (Vit B6) is used for diabetic neuropathy and cyanocobalamine (Vit B12) is required for synthesis of myelin and maintenance of the integrity of neuronal tissue. We hypothesized that supplementing patients (pts) with these 2 vitamins will prevent CiN. There were 3 pt cohorts depending on the chemotherapy regimen. Pts receiving any taxane enrolled in the taxane cohort (N=46), pts receiving vincristine or vinblastine enrolled in the vinca cohort (N=7), and all other pts receiving a platinum enrolled in the heavy metal cohort (N=25). The taxane cohort is reported here. Methods: Pts starting treatment with a taxane were randomized to a 1/6 of 100% of the daily recommended dose of a multivitamin/day (placebo) versus the same plus Vit B6, 50 mg tid, and Vit B12, 1 mg q 3–4 weeks (MV+Vit), during 4 cycles of chemotherapy. No other supplements were allowed. Taxane Fact G and a formal neurologic examination were performed prior to, and after 2 & 4 cycles of chemotherapy. Statistical methods were based on least squared means with ANCOVA and t-test (Cella, JCO, 2008). Results: To date, 46 pts treated with taxanes were randomized; 22 to placebo and 24 to MV+Vit. 13 and 16 pts completed 2 cycles and 8 and 6 pts completed 4 cycles, respectively. On the neuro examination, the only significant difference between placebo and MV+Vit was in the cold sensation (p=0.0097). The physical well being and the neuro modules of the Taxane Fact G significantly worsened after 4 cycles of chemotherapy in the placebo group (p=0.0289 and 0.0173, respectively), but this significant trend was not observed in the MV+Vit group (p=0.8318 and p=0.0866). The study will accrue 76 pts per cohort. Conclusions: The preliminary trends in this study suggest that vitamin supplementation with Vit B6 and B12 may reduce CiN during taxane-based chemotherapy. No significant financial relationships to disclose.

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Villalva-Servín, Nidia P., Alain Laurent, and Alex G. Fallis. "Part 2: Efficient strategies for the construction of variably substituted bicyclo[5.3.1]undecenones (AB-taxane ring systems) and their conversion to tricyclo[9.3.1.03,8]pentadecenones (ABC taxane ring systems) and bicyclo[2.2.2]octanones." Canadian Journal of Chemistry 82, no. 2 (February 1, 2004): 227–39. http://dx.doi.org/10.1139/v03-201.

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The extension of our strategies for the construction of cyclic molecules containing variably substituted bicyclo[5.3.1]undecenones (AB taxane ring systems) for the synthesis of the tricyclo[9.3.1.03,8]pentadecenone (ABC taxane ring system) and bicyclo[2.2.2]octanones are described. These routes employ a multi-component coupling protocol that employs sequential magnesium-mediated carbometallation of allyl-substituted propargyl alcohols followed by diastereoselective Lewis acid catalyzed intramolecular DielsAlder reactions (IMDA). Subsequent ring-closing metathesis (RCM) afforded the ABC taxane core structure. Enone accelerated [3,3] sigmatropic rearrangements (Cope rearrangements) generated the bicyclo[2.2.2]octanone nucleus. In the presence of a Lewis acid, the dienophile precursor underwent a tandem reaction via the adduct directly to the bicyclo[2.2.2]octanones. This is the first example of a novel enone accelerated carbocycle Cope rearrangement and provides direct access to bicyclo[2.2.2]octanones by a new route that compliments the traditional cyclohexadiene cycloaddition approach. Key words: magnesium chelate, Lewis acid, taxanes, DielsAlder, sigmatropic rearrangement, oxy-Cope, ring-closing metathesis, bicyclo[2.2.2]octanone.

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Swindell, Charles S., and Weiming Fan. "Taxane Synthesis through Intramolecular Pinacol Coupling at C-1−C-2. Highly Oxygenated C-Aromatic Taxanes." Journal of Organic Chemistry 61, no. 3 (January 1996): 1109–18. http://dx.doi.org/10.1021/jo9519367.

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Swindell, Charles S., and Weiming Fan. "Taxane Synthesis through Intramolecular Pinacol Coupling at C-1−C-2. Highly Oxygenated C-Aromatic Taxanes." Journal of Organic Chemistry 61, no. 15 (January 1996): 5190. http://dx.doi.org/10.1021/jo964008w.

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6

SWINDELL, C. S., and W. FAN. "ChemInform Abstract: Taxane Synthesis Through Intramolecular Pinacol Coupling at C-1-C-2. Highly Oxygenated C-Aromatic Taxanes." ChemInform 27, no. 27 (August 5, 2010): no. http://dx.doi.org/10.1002/chin.199627200.

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Fenoglio, Ivana, Gian Mario Nano, David G. Vander Velde, and Giovanni Appendino. "Synthesis of azetidine-type taxanes." Tetrahedron Letters 37, no. 18 (April 1996): 3203–6. http://dx.doi.org/10.1016/0040-4039(96)00495-9.

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8

Kende, Andrew S., Stephen Johnson, Pauline Sanfilippo, John C. Hodges, and Louis N. Jungheim. "Synthesis of a taxane triene." Journal of the American Chemical Society 108, no. 12 (June 1986): 3513–15. http://dx.doi.org/10.1021/ja00272a060.

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9

Wei, Chang-Qing, Gang Zhao, Xiang-Rong Jiang, and Yu Ding. "New ring construction strategy in taxane synthesis: stereocontrolled synthesis of taxane CB-ring system." Journal of the Chemical Society, Perkin Transactions 1, no. 23 (1999): 3531–36. http://dx.doi.org/10.1039/a904382i.

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10

Battaglia, Arturo, Eleonora Baldelli, Ezio Bombardelli, Giacomo Carenzi, Gabriele Fontana, Maria Luisa Gelmi, Andrea Guerrini, and Donato Pocar. "Selective synthesis of 14β-amino taxanes." Tetrahedron 61, no. 32 (August 2005): 7727–45. http://dx.doi.org/10.1016/j.tet.2005.05.087.

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Dissertations / Theses on the topic "Taxane synthesis][Synthesis of taxanes"

1

Berry, N. M. "Synthetic approaches to taxanes." Thesis, University of Oxford, 1987. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.379891.

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Harrison, A. G. "Synthesis amongst taxanes." Thesis, University of Nottingham, 1986. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.371125.

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Clark, Jonathan. "New synthetic methods towards the synthesis of taxanes." Thesis, University of Leicester, 1994. http://hdl.handle.net/2381/34051.

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This thesis is a continuation of previous work done in the Jenkins group to produce taxanes from glucose. The reactions investigated by R. Bonnert and J. Howarth are improved upon to enable the large scale synthesis of the diol (1). After the successful protection of (1) with two tert-butyldiphenylsilyl protecting groups the benzylidene ring was opened by bromination with N-bromosuccinimide. This compound then underwent fragmentation with zinc metal to open the acetal ring and yield the highly functionalised key intermediate chiral cyclohexane (2). This aldehyde was then reduced with sodium borohydride and protected with a triethylsilyl group. The alkene side chain underwent ozonolysis cleanly followed by the addition of lithium-2,2,3,3-tetramethyl-bromocyclopropane. The cyclopropane addition was improved upon by the addition of cerium trichloride. Compounds (3) were isolated from this reaction and a series of studies were done to test the viability of these compounds to undergo further reactions, in particular to rearrange to give dienes. Compounds with bromine in were found to rearrange and those with chlorine in did not. It is believed that most of this work was done with compounds containing chlorine, although at the time this was not realised. Detailed spectroscopic studies verified the stereostructures as those desired for taxanes at the key chiral centres. Alternative sugar routes were also considered and this work gave rise to a new Robinson reaction on a carbohydrate, to give compound (4). Unfortunately this compound was found to have the wrong stereostructure for the synthesis of taxanes from it.

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4

Chang, Edcon. "Synthesis of taxane cyclization precursors." Thesis, Massachusetts Institute of Technology, 1997. http://hdl.handle.net/1721.1/43388.

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Mahaney, Paige E. (Paige Erin). "Efforts toward the synthesis of taxane natural products." Thesis, Massachusetts Institute of Technology, 1996. http://hdl.handle.net/1721.1/38760.

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6

Kreilein, Matthew M. "Progress toward the total synthesis of paclitaxel (taxol)." The Ohio State University, 2005. http://rave.ohiolink.edu/etdc/view?acc_num=osu1117063322.

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7

Magnus, Nicholas Andrew. "Synthesis of the anthraquinone portion of dynemicin A : Taxanes chiral construction of the A, B and C rings of taxol." Thesis, University of Bristol, 1996. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.319045.

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8

Phillips, Andrew John. "Synthetic studies on the taxane diterpenoids." Thesis, University of Canterbury. Chemistry, 1999. http://hdl.handle.net/10092/7255.

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This thesis describes synthetic studies aimed towards developing a concise synthesis of taxinine, a member of the taxane class of natural products. In Chapter One, an overview of the strategies used for the synthesis of this class of compounds is provided. A bicyclic enone was identified as a target for the studies described in this thesis. The strategy described also called for the addition of the C-ring by ring-closing metathesis. A six step sequence to a C12-desmethyl A-ring is described in Chapter Two. The key step is the isomerization of an epoxide to an allylic alcohol. It was not possible to extend this chemistry to include C12-methylated substrates. An alternative Diels-Alder approach is also described. This approach allowed the synthesis of a number of C12-methylated A-ring structures. A concise synthesis of diene precursors suitable for exploring the possibility of RCM as a method for the ring closure to form a taxane AB-ring system is described in Chapter Three. The planned ring-closing metathesis reaction was unsuccessful under a number of conditions examined. An investigation described in Chapter Four delineates the use of ring-closing metathesis as a possible method for the introduction of the C-ring onto suitable AB-ring systems. An alternative to the unsuccessful ring-closing metathesis approach, an intramolecular Diels-Alder synthesis of a bicyclo[4.3.1]decene system, is described in Chapter Five. Preliminary investigations into the ring-expansion of this compound are also described. A brief summary and discussion of the future potential of the research conducted in this thesis is provided in Chapter Six.

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9

Green, Andrew D. "Synthetic studies towards the taxane tricycle." Thesis, University of Nottingham, 1995. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.262658.

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GUIR, FREDERIC. "Contribution a la synthese totale du taxol." Paris 11, 1990. http://www.theses.fr/1990PA112038.

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Ce travail se divise en deux parties: la premiere partie s'attache a l'etude de la formation des cycles b et c du taxane sur un modele ainsi que de la stereochimie de la jonction de ces cycles b/c par voie photochimique. Le produit final obtenu: la 14,14-dimethyl-tricyclo 9. 2. 1. 0#3#,#8 tetradecanedione-2,10 possede la jonction de cycle trans 3,8 inverse de celle du taxane. La deuxieme partie decrit la synthese de la dihydroxy-2,12 trimethyl-4,8,11 tricyclo 5. 3. 1. 1#4#,#1#1 dodecene-8 one-5 qui par retroaldolisation conduirait a la formation du systeme bicyclo 5. 3. 1 undecene a/b du taxol, possedant des groupements oxygenes aptes a permettre l'annelation du cycle c. La synthese de ce systeme tricyclique decrite dans cette partie repose sur une condensation intramoleculaire de claisen de l'(oxo-10 hydroxy-7 trimethyl-1,3,9 cis bicyclo 4. 4. 0 decene-3 yl-2) acetate de methyle qui provient de l'adduit de diels-alder, le (dioxo-7,10 trimethyl-1,3,9 cis bicyclo 4. 4. 0 decadiene-3,8 yl-2) acetate de methyle, entre le methyl-4 hexadiene-3,5 oate de methyle et la dimethyl-2,6 para-benzoquinone. L'hydroxy-5 trimethyl-4,8,11 epoxy-2,5 tricyclo 5. 3. 1. 1#4#,#1#1 dodecene-8 one-12 ainsi produit conduit a la dihydroxy-2,12 trimethyl-4,8,11 tricyclo 5. 3. 1. 1#4#,#1#1 dodecene-8 one-5 dont la retroaldolisation s'est revelee infructueuse. La fragmentation de la liaison c-12-c-4 par l'amidure de sodium sur la cetone en c-12 non enolisable a fourni le trimethyl 4,8,11 epoxy-2,5 bicyclo 5. 3. 1 undecadiene-3,8 carboxamide-11 desire

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Book chapters on the topic "Taxane synthesis][Synthesis of taxanes"

1

Paquette, Leo A., Mangzhu Zhao, Francis Montgomery, Qingbei Zeng, Ting Zhong Wang, Steven Elmore, Keith Combrink, Hui-Ling Wang, Simon Bailey, and Zhuang Su. "From D-Camphor to the Taxanes. Highly Concise Rearrangement- Based Approaches to Taxusin and Taxol." In Current Trends in Organic Synthesis, 25–34. Boston, MA: Springer US, 1999. http://dx.doi.org/10.1007/978-1-4615-4801-0_4.

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2

Chen, Jin, Larisa V. Kuznetsova, Ioana M. Ungreanu, and Iwao Ojimau. "Recent Advances in the Synthesis of α-Hydroxy-β-Amino Acids and Their Use in the SAR Studies of Taxane Anticancer Agents." In Enantioselective Synthesis of β-Amino Acids, 447–76. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2005. http://dx.doi.org/10.1002/0471698482.ch19.

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3

Kadow, John F., Thomas Alstadt, Shu-Hui Chen, Pierre Dextraze, Karen Du, Craig Fairchild, Jerzy Golik, et al. "Some Recent Developments in the Synthesis and Structure-Activity Relationship of Novel Taxanes." In Anticancer Agents, 43–58. Washington, DC: American Chemical Society, 2001. http://dx.doi.org/10.1021/bk-2001-0796.ch003.

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4

Swindell, Charles S. "Chemical Studies of the Taxane Diterpenes." In Stereoselective Synthesis, 179–231. Elsevier, 1993. http://dx.doi.org/10.1016/b978-0-444-89366-6.70012-5.

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5

Taber, Douglass F. "C–H Functionalization: The Hatakeyama Synthesis of (–)-Kaitocephalin." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0020.

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John F. Hartwig of the University of California, Berkeley showed (Nature 2012, 483, 70) that intramolecular C–H silylation of 1 selectively gave, after oxidation and acetylation, the bis acetate 2. Gong Chen of Pennsylvania State University coupled (J. Am. Chem. Soc. 2012, 134, 7313) 3 with 4 to give the ether 5. M. Christina White of the University of Illinois effected (J. Am. Chem. Soc. 2012, 134, 9721) selective oxidation of the taxane derivative 6 to the lactone 7. Most of the work on C–H functionalization has focused on the formation of C–C, C–O, and C–N bonds. Donald A. Watson of the University of Delaware developed (Angew. Chem. Int. Ed. 2012, 51, 3663) conditions for the complementary conversion of an alkene 8 to the allyl silane 9, a powerful and versatile nucleophile. Kilian Muniz of ICIQ Tarragona oxidized (J. Am. Chem. Soc. 2012, 134, 7242) the enyne 10 selectively to the amine 11. Phil S. Baran of Scripps/La Jolla devised (J. Am. Chem. Soc. 2012, 134, 2547) a protocol for the OH-directed amination of 12 to 13. Professor White developed (J. Am. Chem. Soc. 2012, 134, 2036) a related OH-directed amination of 14 to 15 that proceeded with retention of absolute configuration. Tom G. Driver of the University of Illinois, Chicago showed (J. Am. Chem. Soc. 2012, 134, 7262) that the aryl azide 16 could be cyclized directly to the amine, which was protected to give 17. As illustrated by the conversion of 18 to 20 devised (Adv. Synth. Catal. 2012, 354, 701) by Martin Klussmann of the Max-Planck-Institut, Mülheim, C–H functionalization can be accomplished by hydride abstraction followed by coupling of the resulting carbocation with a nucleophile. Olafs Daugulis of the University of Houston used (Angew. Chem. Int. Ed. 2012, 51, 5188) a Pd catalyst to couple 21 with 22 to give 23 with high diastereocontrol. Yoshiji Takemoto of Kyoto University cyclized (Angew. Chem. Int. Ed. 2012, 51, 2763) the chloroformate 24 directly to the oxindole 25.

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Conference papers on the topic "Taxane synthesis][Synthesis of taxanes"

1

Fang, Weishuo. "Abstract 4416: Pursuing semi-synthetic taxanes as antitumor agents effective against drug-resistant tumors." In Proceedings: AACR 101st Annual Meeting 2010‐‐ Apr 17‐21, 2010; Washington, DC. American Association for Cancer Research, 2010. http://dx.doi.org/10.1158/1538-7445.am10-4416.

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