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

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Published: 4 June 2021

Last updated: 16 February 2022

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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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2

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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3

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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4

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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5

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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7

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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11

Mendoza, Abraham, Yoshihiro Ishihara, and Phil S. Baran. "Scalable enantioselective total synthesis of taxanes." Nature Chemistry 4, no. 1 (November 6, 2011): 21–25. http://dx.doi.org/10.1038/nchem.1196.

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12

Muller, Benoît, Francette Delaloge, Marc den Hartog, Jean-Pierre Férézou, Ange Pancrazi, Joëlle Prunet, Jean-Yves Lallemand, Alain Neuman, and Thierry Prangé. "Diastereoselective synthesis of a taxane precursor." Tetrahedron Letters 37, no. 19 (May 1996): 3313–16. http://dx.doi.org/10.1016/0040-4039(96)00538-2.

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13

Bourgeois, Damien, Jean-Yves Lallemand, Ange Pancrazi, and Joëlle Prunet. "Diastereoselective Synthesis of a seco-Taxane." Synlett 1999, no. 10 (December 31, 1999): 1555–58. http://dx.doi.org/10.1055/s-1999-2889.

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14

Swindell, Charles S. "TAXANE DITERPENE SYNTHESIS STRATEGIES. A REVIEW." Organic Preparations and Procedures International 23, no. 4 (August 1991): 465–543. http://dx.doi.org/10.1080/00304949109458240.

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15

OHTSUKA, YASUO, and TAKESHI OISHI. "Studies on taxane synthesis. I. Synthesis of 3,8,11,11-tetramethyl-4-oxobicyclo[5.3.1]undecane as a model for taxane synthesis." CHEMICAL & PHARMACEUTICAL BULLETIN 36, no. 12 (1988): 4711–21. http://dx.doi.org/10.1248/cpb.36.4711.

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16

Wei, Chang-Qing, Gang Zhao, Xiang-Rong Jiang, and Yu Ding. "ChemInform Abstract: New Ring Construction Strategy in Taxane Synthesis: Stereocontrolled Synthesis of Taxane CB-Ring System." ChemInform 31, no. 20 (June 8, 2010): no. http://dx.doi.org/10.1002/chin.200020155.

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17

Boa, A. N., P. R. Jenkins, and N. J. Lawrence. "Recent progress in the synthesis of taxanes." Contemporary Organic Synthesis 1, no. 1 (1994): 47. http://dx.doi.org/10.1039/co9940100047.

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18

Ishihara, Yoshihiro, Abraham Mendoza, and Phil S. Baran. "Total synthesis of taxane terpenes: cyclase phase." Tetrahedron 69, no. 27-28 (July 2013): 5685–701. http://dx.doi.org/10.1016/j.tet.2013.04.028.

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19

Klein, Larry L., Clarence J. Maring, Leping Li, Clinton M. Yeung, Sheela A. Thomas, David J. Grampovnik, J. J. Plattner, and Rodger F. Henry. "Synthesis of Ring B-Rearranged Taxane Analogs." Journal of Organic Chemistry 59, no. 9 (May 1994): 2370–73. http://dx.doi.org/10.1021/jo00088a017.

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20

Liang, Xiao-Xia, Pei Tang, Qiao-Hong Chen, and Feng-Peng Wang. "Synthesis of Taxane ABC Tricyclic Skeleton from Lycoctonine." Natural Product Communications 7, no. 6 (June 2012): 1934578X1200700. http://dx.doi.org/10.1177/1934578x1200700603.

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A new conversional synthesis of the ABC ring system of taxoids from the C19-diterpenoid alkaloid lycoctonine was developed in 6 steps with 2% overall yield. The distinctive features of the conversion include pinacol rearrangement, enlargement of ring B, and opening of a four-membered ring.

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21

Ali, Shaukat, Imran Ahmad, Andrew Peters, Gregg Masters, Sharma Minchey, Andrew Janoff, and Eric Mayhew. "Hydrolyzable hydrophobic taxanes: synthesis and anti-cancer activities." Anti-Cancer Drugs 12, no. 2 (February 2001): 117–28. http://dx.doi.org/10.1097/00001813-200102000-00004.

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22

Dambruoso, Paolo, Carla Bassarello, Giuseppe Bifulco, Giovanni Appendino, Arturo Battaglia, Andrea Guerrini, Gabriele Fontana, and Luigi Gomez-Paloma. "2′-Methyl taxanes: synthesis and NMR configurational assignment." Tetrahedron Letters 46, no. 19 (May 2005): 3411–15. http://dx.doi.org/10.1016/j.tetlet.2005.03.095.

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23

Yuan, Changxia, Yehua Jin, Nathan C. Wilde, and Phil S. Baran. "Short, Enantioselective Total Synthesis of Highly Oxidized Taxanes." Angewandte Chemie International Edition 55, no. 29 (May 30, 2016): 8280–84. http://dx.doi.org/10.1002/anie.201602235.

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24

Yuan, Changxia, Yehua Jin, Nathan C. Wilde, and Phil S. Baran. "Short, Enantioselective Total Synthesis of Highly Oxidized Taxanes." Angewandte Chemie 128, no. 29 (May 30, 2016): 8420–24. http://dx.doi.org/10.1002/ange.201602235.

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25

Pérez-Estrada, S., N. Sayar, and J. R. Granja. "Towards taxane analogues synthesis by dienyne ring closing metathesis." Organic Chemistry Frontiers 3, no. 10 (2016): 1331–36. http://dx.doi.org/10.1039/c6qo00321d.

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26

Klein, Larry L. "Synthesis of 9-dihydrotaxol: A novel bioactive taxane." Tetrahedron Letters 34, no. 13 (March 1993): 2047–50. http://dx.doi.org/10.1016/s0040-4039(00)60342-8.

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27

Benchikh le-Hocine, M., D. Do Khac, and M. Fetizon. "Model Studies in Taxane Diterpene Synthesis. Part III." Synthetic Communications 22, no. 2 (January 1992): 245–55. http://dx.doi.org/10.1080/00397919208021299.

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28

Bonnert, Roger V., and Paul R. Jenkins. "A synthesis of an alkylated taxane model system." Journal of the Chemical Society, Perkin Transactions 1, no. 3 (1989): 413. http://dx.doi.org/10.1039/p19890000413.

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29

SWINDELL, C. S. "ChemInform Abstract: Taxane Diterpene Synthesis Strategies. A Review." ChemInform 23, no. 6 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199206314.

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30

MULLER, B., F. DELALOGE, M. DEN HARTOG, J. P. FEREZOU, A. PANCRAZI, J. PRUNET, J. Y. LALLEMAND, A. NEUMAN, and T. PRANGE. "ChemInform Abstract: Diastereoselective Synthesis of a Taxane Precursor." ChemInform 27, no. 33 (August 5, 2010): no. http://dx.doi.org/10.1002/chin.199633206.

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31

Schneider, Fabian, Konstantin Samarin, Simone Zanella, and Tanja Gaich. "Total synthesis of the complex taxane diterpene canataxpropellane." Science 367, no. 6478 (February 6, 2020): 676–81. http://dx.doi.org/10.1126/science.aay9173.

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Canataxpropellane belongs to the medicinally important taxane diterpene family. The most prominent congener, Taxol, is one of the most commonly used anticancer agent in clinics today. Canataxpropellane exhibits a taxane skeleton with three additional transannular C–C bonds, resulting in a total of six contiguous quaternary carbons, of which four are located on a cyclobutane ring. Unfortunately, isolation of canataxpropellane from natural sources is inefficient. Here, we report a total synthesis of (–)-canataxpropellane in 26 steps and 0.5% overall yield from a known intermediate corresponding to 29 steps from commercial material. The core structure of the (–)-canataxpropellane (2) was assembled in two steps using a Diels–Alder/ortho-alkene-arene photocycloaddition sequence. Enantioselectivity was introduced by designing chiral siloxanes to serve as auxiliaries in the Diels–Alder reaction.

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32

Tarrant, James G., Donald Cook, Craig Fairchild, John F. Kadow, Byron H. Long, William C. Rose, and Dolatrai Vyas. "Synthesis and biological activity of macrocyclic taxane analogues." Bioorganic & Medicinal Chemistry Letters 14, no. 10 (May 2004): 2555–58. http://dx.doi.org/10.1016/j.bmcl.2004.02.086.

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33

Kanda, Yuzuru, Yoshihiro Ishihara, Nathan C. Wilde, and Phil S. Baran. "Two-Phase Total Synthesis of Taxanes: Tactics and Strategies." Journal of Organic Chemistry 85, no. 16 (July 14, 2020): 10293–320. http://dx.doi.org/10.1021/acs.joc.0c01287.

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34

BOA, A. N., P. R. JENKINS, and N. J. LAWRENCE. "ChemInform Abstract: Recent Progress in the Synthesis of Taxanes." ChemInform 25, no. 52 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199452290.

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35

Georg, Gunda I., Geraldine C. B. Harriman, Michael Hepperle, Jamie S. Clowers, David G. Vander Velde, and Richard H. Himes. "Synthesis, Conformational Analysis, and Biological Evaluation of Heteroaromatic Taxanes." Journal of Organic Chemistry 61, no. 8 (January 1996): 2664–76. http://dx.doi.org/10.1021/jo951961c.

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36

Swindell, Charles S., and Bomi P. Patel. "Synthesis and stereochemistry of a saturated tricyclic taxane model." Tetrahedron Letters 28, no. 44 (January 1987): 5275–78. http://dx.doi.org/10.1016/s0040-4039(00)96706-6.

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37

KLEIN, L. L., C. J. MARING, L. LI, C. M. YEUNG, S. A. THOMAS, D. J. GRAMPOVNIK, J. J. PLATTNER, and R. F. HENRY. "ChemInform Abstract: Synthesis of Ring B-Rearranged Taxane Analogues." ChemInform 25, no. 43 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199443229.

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38

Montalbetti, C. "A Convergent Synthesis of Functionalized B-seco Taxane Skeletons." Tetrahedron Letters 36, no. 33 (August 14, 1995): 5891–94. http://dx.doi.org/10.1016/00404-0399(50)1172e-.

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39

Magnus, Philip, John Booth, Louis Diorazio, Timothy Donohoe, Vince Lynch, Nicholas Magnus, José Mendoza, Philip Pye, and James Tarrant. "Taxane diterpenes 2: Synthesis of the 7-deoxy ABC taxane skeleton, and reactions of the A-ring." Tetrahedron 52, no. 45 (November 1996): 14103–46. http://dx.doi.org/10.1016/0040-4020(96)00866-6.

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40

Hirai, Yoshimasa, and Hiroto Nagaoka. "Synthesis of taxane ring by intramolecular nitrile oxide cyclization reaction." Tetrahedron Letters 38, no. 11 (March 1997): 1969–70. http://dx.doi.org/10.1016/s0040-4039(97)00236-0.

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41

GHOSH, S., and S. SARKAR. "ChemInform Abstract: Recent Developments in the Synthesis of Taxane Diterpenes." ChemInform 26, no. 25 (August 17, 2010): no. http://dx.doi.org/10.1002/chin.199525261.

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42

Mäding, P., J. Zessin, U. Pleiß, F. Füchtner, and F. Wüst. "Synthesis of a11C-labelled taxane derivative by [1-11C]acetylation." Journal of Labelled Compounds and Radiopharmaceuticals 49, no. 4 (2006): 357–65. http://dx.doi.org/10.1002/jlcr.1059.

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43

Winkler, Jeffrey D., Joanne M. Holland, and David A. Peters. "Synthesis of Cyclopropyl Taxane Analogs via Sequential Diels−Alder Reactions." Journal of Organic Chemistry 61, no. 26 (January 1996): 9074–75. http://dx.doi.org/10.1021/jo961617v.

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44

PAQUETTE, L. A. "ChemInform Abstract: Studies Directed Toward the Total Synthesis of the Taxanes." ChemInform 24, no. 28 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199328311.

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45

Winkler, Jeffrey D., John P. Hey, and Stephen D. Darling. "Studies directed towards the synthesis of taxane diterpenes: A remarkable rearrangement." Tetrahedron Letters 27, no. 49 (January 1986): 5959–62. http://dx.doi.org/10.1016/s0040-4039(00)85372-1.

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46

KLEIN, L. L. "ChemInform Abstract: Synthesis of 9-Dihydrotaxol (I): A Novel Bioactive Taxane." ChemInform 24, no. 34 (September 1, 2010): no. http://dx.doi.org/10.1002/chin.199334245.

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47

Ma, Cong, Aurélien Letort, Rémi Aouzal, Antonia Wilkes, Gourhari Maiti, Louis J. Farrugia, Louis Ricard, and Joëlle Prunet. "Cascade Metathesis Reactions for the Synthesis of Taxane and Isotaxane Derivatives." Chemistry - A European Journal 22, no. 20 (April 8, 2016): 6891–98. http://dx.doi.org/10.1002/chem.201600592.

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48

Reuß, Franziska, and Philipp Heretsch. "Taxane Meets Propellane: First Chemical Synthesis of Highly Complex Diterpene Canataxpropellane." Angewandte Chemie International Edition 59, no. 26 (April 16, 2020): 10232–34. http://dx.doi.org/10.1002/anie.202002118.

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49

MONTALBETTI, C., M. SAVIGNAC, F. BONNEFIS, and J. P. GENET. "ChemInform Abstract: A Convergent Synthesis of Functionalized B-seco Taxane Skeletons." ChemInform 26, no. 48 (August 17, 2010): no. http://dx.doi.org/10.1002/chin.199548202.

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50

DeMattei, John A., M. Robert Leanna, Wenke Li, Paul J. Nichols, Michael W. Rasmussen, and Howard E. Morton. "An Efficient Synthesis of the Taxane-Derived Anticancer Agent ABT-271." Journal of Organic Chemistry 66, no. 10 (May 2001): 3330–37. http://dx.doi.org/10.1021/jo0057203.

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