Relevant bibliographies by topics / Taxol - Synthesis

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  1. Journal articles
  2. Dissertations / Theses
  3. Books
  4. Book chapters
  5. Conference papers
  6. Reports

Academic literature on the topic 'Taxol - Synthesis'

Author: Grafiati
Published: 4 June 2021
Last updated: 6 September 2023

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Journal articles on the topic "Taxol - Synthesis"

1

Taylor, George F., Stephen S. Thornton, C. Ray Tallent, and John A. Kepler. "Synthesis of [3″-3H]taxol and [13-3H]taxol1." Journal of Labelled Compounds and Radiopharmaceuticals 33, no. 6 (1993): 501–15. http://dx.doi.org/10.1002/jlcr.2580330608.

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Blume, E. "Taxol Synthesis in Perspective." JNCI Journal of the National Cancer Institute 84, no. 9 (1992): 674. http://dx.doi.org/10.1093/jnci/84.9.674.

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Nicolaou, K. C., Z. Yang, J. J. Liu, et al. "Total synthesis of taxol." Nature 367, no. 6464 (1994): 630–34. http://dx.doi.org/10.1038/367630a0.

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Jun, C. D., B. M. Choi, H. M. Kim, and H. T. Chung. "Involvement of protein kinase C during taxol-induced activation of murine peritoneal macrophages." Journal of Immunology 154, no. 12 (1995): 6541–47. http://dx.doi.org/10.4049/jimmunol.154.12.6541.

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Abstract Taxol has been known to block cell division by stabilizing microtubules with promising anticancer activity. However, taxol has distinct cell cycle-independent effects. Recently, this novel drug has been shown to provide a second signal for murine macrophage activation to tumoricidal activity via L-arginine-dependent nitric oxide (NO) synthesis. To investigate the mechanism of taxol-induced NO synthesis, we evaluated the ability of protein kinase C (PKC) inhibitors such as staurosporine (STSN) or polymyxin B to block taxol-induced effects. Taxol alone had only a small effect, whereas t
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Utsugi, Masayuki, Mitsuhiro Iwamoto, Sho Hirai, Hatsuo Kawada, and Masahisa Nakada. "Formal Total Synthesis of (−)-Taxol." Journal of Synthetic Organic Chemistry, Japan 75, no. 11 (2017): 1102–14. http://dx.doi.org/10.5059/yukigoseikyokaishi.75.1102.

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Hu, Ya-Jian, Chen-Chen Gu, Xin-Feng Wang, Long Min, and Chuang-Chuang Li. "Asymmetric Total Synthesis of Taxol." Journal of the American Chemical Society 143, no. 42 (2021): 17862–70. http://dx.doi.org/10.1021/jacs.1c09637.

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Hu, Ya-Jian, Chen-Chen Gu, Xin-Feng Wang, Long Min, and Chuang-Chuang Li. "Asymmetric Total Synthesis of Taxol." Journal of the American Chemical Society 143, no. 42 (2021): 17862–70. http://dx.doi.org/10.1021/jacs.1c09637.

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Sun, Dongyu, and Hanfeng Ding. "Asymmetric Total Synthesis of Taxol." Chinese Journal of Organic Chemistry 41, no. 12 (2021): 4827. http://dx.doi.org/10.6023/cjoc202100089.

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MUKAIYAMA, Teruaki, Isamu SHIINA, Hayato IWADARE, et al. "Asymmetric Total Synthesis of Taxol." Proceedings of the Japan Academy. Ser. B: Physical and Biological Sciences 73, no. 6 (1997): 95–100. http://dx.doi.org/10.2183/pjab.73.95.

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Morihira, Koichiro, Ryoma Hara, Shigeru Kawahara, et al. "Enantioselective Total Synthesis of Taxol." Journal of the American Chemical Society 120, no. 49 (1998): 12980–81. http://dx.doi.org/10.1021/ja9824932.

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Dissertations / Theses on the topic "Taxol - Synthesis"

1

Rodriguez, Patricia Fernandez. "Streamlined synthesis of taxol analogues." Thesis, University of Oxford, 2017. https://ora.ox.ac.uk/objects/uuid:58d4a7f3-038e-4c4a-9aec-67267277670f.

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This thesis centres on the synthesis of taxol analogues via late-stage hydroxylation with P450 enzymes. To accomplish this, the taxane core, specifically taxa-4(5),11(12)-dien-2-one, was synthesised by classical synthetic methods, and subsequently oxidised using P450<sub>BM3</sub> mutants. Chapter 1 introduces enzymatic catalysis, and the advantages and disadvantages of its application to organic synthesis. Additionally, an overview of taxol, including its discovery, mode of action, biosynthesis and large-scale production, and a summary of the previously reported approaches to the taxane core
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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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Hofferberth, John E. "Progress toward the total synthesis of Taxol /." The Ohio State University, 2002. http://rave.ohiolink.edu/etdc/view?acc_num=osu1486463321625038.

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Tierney, Jason P. "Stereoselective synthesis of C-glycosidic oxetanes." Thesis, Imperial College London, 1995. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.309528.

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Metaferia, Belhu B. "Synthesis of Taxol™ Analogs as Conformational Probes." Diss., Virginia Tech, 2002. http://hdl.handle.net/10919/28428.

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Taxol™, isolated from the bark of Taxus brevifolia in the late 1960s, and the semisynthetic analog Taxotere™ have proven clinical importance for the treatment of ovarian and breast cancer. Taxol™ exerts its biological effect by binding to polymerized tubulin and stabilizing the resulting microtubules. Studies aimed at understanding the biologically active conformation of taxol and its binding environment on β-tubulin are described. This knowledge is important because it could lead to the design of structurally less complicated drugs with better efficacy and better bioavailability. Moreover
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Zeng, Qingbei. "Studies toward the total synthesis of Taxol®/." The Ohio State University, 1999. http://rave.ohiolink.edu/etdc/view?acc_num=osu1488190595940418.

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Wilkes, Antonia. "Towards the synthesis of the ABC tricycle of Taxol." Thesis, University of Glasgow, 2015. http://theses.gla.ac.uk/5885/.

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Taxol is one of the world’s most successful drugs used in the treatment of cancers. Isolated from the bark of the Pacific yew tree (Taxus brevifolia), it is a molecule of great interest within organic chemistry; with six total syntheses and a number of synthetic works having been published since its discovery. A semi-convergent synthesis of an intermediate in Holton’s synthesis was planned. The overall synthetic plan is shown below. The A ring would be installed by an intramolecular pinacol condensation. The BC bicycle would be closed by ring-closing metathesis at C10-C11. The ketone at C12 wo
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Baloglu, Erkan Jr. "A New Synthesis of Taxol®, from Baccatin III." Thesis, Virginia Tech, 1998. http://hdl.handle.net/10919/36930.

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Taxol®, an important anticancer drug, was first isolated in extremely low yield from the bark of the western yew, Taxus brevifolia. The clinical utility of Taxol has prompted a tremendous effort to obtain this complex molecule synthetically. Due to the chemical complexity of Taxol, its commercial production by total synthesis is not likely to be economical. Another natural product, 10-deacetyl baccatin III, is readily available in higher yield. Several methods have been reported for the synthesis of Taxol by coupling baccatin III and the N-benzoyl-β-phenylisoserine side chain. A new method
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Tsui, Hon-Chung. "Studies on the synthesis of Kaurane Diterpenoids and Taxol /." The Ohio State University, 1998. http://rave.ohiolink.edu/etdc/view?acc_num=osu1487951214937412.

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Letort, Aurelien. "Ring-closing metathesis cascade toward a formal synthesis of taxol." Thesis, University of Glasgow, 2015. http://theses.gla.ac.uk/6677/.

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TaxolTM and its derivatives are the largest selling anticancer drugs of all time. Numerous synthetic works and total syntheses have been published since its discovery, but to date no high yielding synthesis with less than 37 steps has been achieved. In this thesis is presented our synthetic efforts toward such a robust and efficient synthesis of Taxol. The optimisation of the Shapiro coupling fragments syntheses were investigated to enhance the robustness of our strategy. Then the C7-deoxy model ABC tricycle ring-system of Taxol, which lacks the oxygenated substituent at C7, has been efficient
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Books on the topic "Taxol - Synthesis"

1

Ducki, Sylvie. The semi-synthesis of taxol. UMIST, 1994.

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Collet, E. Studies of the anti-cancer drug Taxol synthesis of the C-13 side chain. UMIST, 1993.

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Li, Jie Jack. Top Drugs. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780199362585.001.0001.

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Drugs like Lipitor, Plavix, Taxol, and Zoloft are integral in today's medicinal world. These widely used products save lives and improve the quality of lives, playing a crucial role in everything from cholesterol management to cancer treatment. These advances in medicine were brought into existence after nuanced process of creation, featuring a wide range of chemical and pharmacological experimentation and discovery. Top Drugs: Their History, Pharmacology, and Synthesis provides an in-depth study on ten prominent drugs, outlining the chemistry behind each one's creation. Jie Jack Li, a medicin
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Book chapters on the topic "Taxol - Synthesis"

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Wender, Paul A., Michael G. Natchus, and Anthony J. Shuker. "Toward the Total Synthesis of Taxol and its Analogues." In TAXOL®. CRC Press, 2021. http://dx.doi.org/10.1201/9780138737361-8.

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Paquette, Leo A., Mangzhu Zhao, Francis Montgomery, et al. "From D-Camphor to the Taxanes. Highly Concise Rearrangement- Based Approaches to Taxusin and Taxol." In Current Trends in Organic Synthesis. Springer US, 1999. http://dx.doi.org/10.1007/978-1-4615-4801-0_4.

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Nakada, Masahisa. "Enantioselective Total Synthesis of the Antitumor Polycyclic Natural Products FR182877 and Taxol." In Cutting-Edge Organic Synthesis and Chemical Biology of Bioactive Molecules. Springer Singapore, 2019. http://dx.doi.org/10.1007/978-981-13-6244-6_3.

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Lee, Sang-Hyeup, Juyoung Yoon, Kensuke Nakamura, and Yoon-Sik Lee. "Preparation of β-Amino-α-mercapto Acids and Amides: Stereocontrolled Syntheses of 2′-Sulfur Analogues of the Taxol C-13 Side Chain, Both syn and and S-Acetyl-N-benzoyl-3-phenylisocysteine." In Peptides: The Wave of the Future. Springer Netherlands, 2001. http://dx.doi.org/10.1007/978-94-010-0464-0_19.

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Taber, Douglass F. "The Sato/Chida Synthesis of Paclitaxel (Taxol®)." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0104.

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Paclitaxel (Taxol®) 3 is widely used in the clinical treatment of a variety of cancers. Takaaki Sato and Noritaka Chida of Keio University envisioned (Org. Lett. 2015, 17, 2570, 2574) establishing the central eight-membered ring of 3 by the SmI2-mediated cyclization of 1 to 2. The starting point for the synthesis was the enantiomerically-pure enone 5, pre­pared from the carbohydrate precursor 4. Conjugate addition to 5 proceeded anti to the benzyloxy substituent to give, after trapping with formaldehyde and protection, the ketone 6. Reduction and protection followed by hydroboration led to 7, that was, after protection and deprotection, oxidized to 8. The second ring of 3 was added in the form of the alkenyl lithium derivative 9, prepared from the trisylhydrazone of the corresponding ketone. Hydroxyl-directed epoxidation of 10 proceeded with high facial selectivity, leading, after reduction and protection, to the cyclic carbonate 11. Allylic oxidation converted the alkene into the enone, while at the same time oxidizing the benzyl protecting group to the ben­zoate, to give 12. Reduction of the ketone 12 led to a mixture of diastereomers. In practice, only one of the diastereomers of 1 cyclized cleanly to 2, as illustrated, so the undesired diastereomer from the NaBH4 reduction was oxidized back to the enone for recycling. For convenience, only one of the diastereomers of 2 was carried forward. To establish the tetrasubstituted alkene of 3, the alkene of 2 was converted to the cis diol and on to the bis xanthate 13. Warming to 50°C led to the desired tet­rasubstituted alkene, sparing the oxygenation that is eventually required for 3. For convenience, to intercept 16, the intermediate in the Takahashi total synthesis, both xanthates were eliminated to give 14. Hydrogenation removed the disubsti­tuted alkene, and also deprotected the benzyl ether. Oxidation followed by Peterson alkene formation led to 15, that was carried on to the Takahashi intermediate 16 using the now-standard protocol for oxetane construction. It is a measure of the strength of the science of organic synthesis that Masahisa Nakada of Waseda University also reported (Chem. Eur. J. 2015, 21, 355) an elegant synthesis of 3 (not illustrated).
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Cordes, Eugene H. "The discovery of taxol: Wall, Horwitz, Holton." In Hallelujah Moments. Oxford University Press, 2020. http://dx.doi.org/10.1093/oso/9780190080457.003.0007.

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Taxol is a widely employed drug for chemotherapy of breast cancer and finds use for ovarian and lung cancer as well as for Kaposi’s syndrome. Getting from the discovery of taxol to approval for treatment of cancer took 30 years. The molecule was discovered in the Pacific yew tree, where it occurs in very small amounts. Early studies proved encouraging but not striking enough to generate real enthusiasm for pushing taxol forward. Then Susan Horwitz discovered its mechanism of action—it prevents the dissolution of microtubules—and enthusiasm strengthened. The problem at that stage was getting enough taxol to treat patients. Environmentalists were concerned that harvesting trees for taxol would destroy basically all of the Pacific yew trees in old forests, a legitimate concern. The discovery of a taxol precursor in the English yew, where it occurs in substantial amounts, coupled with the synthesis of taxol from that precursor solved the supply issue. It is now made by total synthesis. Determination by a few scientists over decades brought this important cancer drug into practice.
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Holton, Robert A. "Total Synthesis of Taxusin: An Initial Step Toward Taxol Synthesis." In Strategies and Tactics in Organic Synthesis. Elsevier, 1991. http://dx.doi.org/10.1016/b978-0-08-092430-4.50011-1.

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Taber, Douglass. "The Betzer and Ardisson Synthesis of (+)-Discodermolide." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0085.

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( + )-Discodermolide 3, a potent anticancer agent that works synergistically with taxol, may yet prove to be clinically effective. For the synthetic material to be affordable, a highly convergent synthesis is required. Jean-François Betzer and Janick Ardisson of the Université de Cergy- Pontoise have described (Angew. Chem. Int. Ed. 2007, 46, 1917) such a synthesis, coupling 1 and 2. A central feature of their approach was the repeated application of the inherently chiral secondary organometallic reagent 5. The first use of 5 was the addition to the aldehyde 4. The product 6 was ozonized, and the resulting aldehyde was carried on to the α, β-unsaturated ester. Exposure of the hydroxy ester to benzaldehyde under basic conditions delivered, by intramolecular Michael addition, the acetal 7. The next addition of the reagent 5 was to the aldehyde 10. The adduct 11 was deprotonated with t-BuLi to effect α-elimination, providing, after protection of the alcohol, the alkyne 12. Coupling of 12 with the amide 7 gave a ketone, enantioselective reduction of which under Itsuno-Corey conditions led, again after protection of the alcohol, to the alkyne 13. Oxidation followed by selective hydrogenation and iodine-tin exchange then completed the assembly of 1. Note that PtO2, not typically used for partial hydrogenation, was the catalyst of choice for this congested alkyne. The third application of the enantiomerically-pure reagent 5 was addition to the aldehyde that had been prepared by ozonolysis of 15. Advantage was then taken of another property of the alkenyl carbamate, Ni-mediated Grignard coupling, to form the next carbon-carbon bond with high geometric control. Deprotection of the diene 17 so prepared followed by iodination then completed the synthesis of 2. The convergent coupling of 1 with 2 was carried out under Suzuki conditions. Reduction of the iodide of 2 to the corresponding alkyl lithium followed by exchange with B-OMe-9-BBN gave an intermediate organoborane, that smoothly coupled with 1 under Pd catalysis to give 18.
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Taber, Douglass. "The Keck Synthesis of Epothilone B." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0101.

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The total synthesis of Epothilone B 4, the first natural product (with Epothilone A) to show the same microtubule-stabilizing activity as paclitaxel (Taxol®), has attracted a great deal of attention since that activity was first reported in 1995. The total synthesis of 4 devised (J. Org. Chem. 2008, 73, 9675) by Gary E. Keck of the University of Utah was based in large part on the stereoselective allyl stannane additions (e.g. 1 + 2 → 3 ) that his group originated. The allyl stannane 2 was prepared from the acid chloride 5. Exposure of 5 to Et3N generated the ketene, that was homologated with the phosphorane 6 to give the allene ester 7. Cu-mediated conjugate addition of the stannylmethyl anion 8 then delivered 2. The silyloxy aldehyde 1 was prepared from the ester 9 by reduction with Dibal. Felkincontrolled 1,2-addition of the allyl stannane 2 established the relative configuration of the secondary alcohol of 3, that was then used to control the relative configuration of the new alcohol in 10. Addition of the crotyl borane 12 to the derived aldehyde 11 also proceeded with high diastereocontrol. The other component of 4 was prepared from the aldehyde 14. Enantioselective allylation, by the method the authors developed, delivered the alcohol 16. The Z trisubstituted alkene was then assembled by condensing the aldehyde 17 with the phosphorane 18. Dibal reduction of the product lactone 19 gave a diol, the allylic alcohol of which was selectively converted to the chloride with the Corey-Kim reagent. Hydride reduction then delivered the desired homoallylic alcohol, that was converted to the phosphonium salt 21. Condensation of 21 with 13 gave the diene, that was carried on to Epothilone B 4. The synthesis of Epothilone B 4 as originally conceived by the authors depended on ring-closing metathesis of the triene 22. They prepared 22, but on exposure to the second-generation Grubbs catalyst it was converted only to 23. The authors concluded that the trans acetonide kept 22 in a conformation that did not allow the desired macrocyclization.
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Taber, Douglass F. "The Nakada Synthesis of (-)-FR182877." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0084.

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The Streptomyces metabolite (-)-FR182877 3 binds to and stabilizes microtubules, showing the same potency of anticancer activity as Taxol (paclitaxel). Masahisa Nakada of Waseda University assembled (Angew. Chem. Int. Ed. 2009, 48, 2580) the hexacyclic ring system of 3 by the tandem intramolecular Diels-Alder–intramolecular hetero Diels-Alder cyclization of 1, generating seven new stereogenic centers in a single step. The construction of the pentaene substrate 1 started with the known aldehyde 4, prepared by homologation of commercial ethyl 3-methyl-4-oxocrotonate. Addition of the propionyl oxazolidine anion 5 proceeded with high diastereocontrol, to give 6. The acyl oxazolidinone was not an efficient acylating agent, so it was converted to the Weinreb amide. Protection and deprotection then delivered the allylic acetate 7. The key step in the pentaene assembly was the carefully optimized Negishi-Wipf methylation of 8, followed by Pd-mediated coupling of the alkenyl organometallic so generated with the allylic acetate, to give 9. Condensation of the derived keto phosphonate 11 with the known aldehyde 12 then delivered the enone 13. The Nakada group has worked extensively on the intramolecular Diels-Alder reaction of substrates such as 1. They have shown that protected anti diols such as 1 cyclize with substantial diastereocontrol and in the desired sense. In contrast, cyclizations of protected syn diols proceed with poor diastereocontrol. The enone 13 was therefore reduced to the anti diol and protected, leading to 14 . Oxidation of 14 at room temperature led to a complex mixture, but slow oxidation at elevated temperature delivered 2 . Although the yield of 2 was not much better than if the reactions were carried out sequentially, first the intramolecular Diels-Alder cyclization, then the intramolecular hetero Diels-Alder cyclization, with the cascade protocol pure 2 was more readily separated from the reaction matrix. With 2 in hand, there was still the challenge of assembling the seven-membered ring. Cyclization was effected with an intramolecular Heck protocol. The two diastereomers of the allylic alcohol 15 cyclized with comparable efficiency. Ir-catalyzed alkene migration then converted the allylic alcohols to a mixture of ketones, which was equilibrated to give the more stable diasteromer.
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Conference papers on the topic "Taxol - Synthesis"

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Kim, Hyo Jun, Battogtokh Gantumur, Sook Hee Kim, Sumi Bae, and Woong Shick Ahn. "Abstract 3710: Facile Synthesis and Characterization of Pyropheophorbide-a -Taxol Conjugate." 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.am10-3710.

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Marin, M., and D. Craig. "An Asymmetric Synthetic Approach to the A-ring of the Taxol Family of Anti-Cancer Compounds." In The 1st International Electronic Conference on Synthetic Organic Chemistry. MDPI, 1997. http://dx.doi.org/10.3390/ecsoc-1-02034.

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Reports on the topic "Taxol - Synthesis"

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Jo, Hyunil. Synthesis of Taxol-Like Prostate Cancer Chemotherapeutic Agents. Defense Technical Information Center, 2007. http://dx.doi.org/10.21236/ada494576.

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Jo, Hyunil. Synthesis of Taxol-Like Prostate Cancer Chemotherapeutic Agents. Defense Technical Information Center, 2008. http://dx.doi.org/10.21236/ada494578.

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Jo, Hyunil. Synthesis of Taxol-Like Prostate Cancer Chemotherapeutic Agents. Defense Technical Information Center, 2006. http://dx.doi.org/10.21236/ada463455.

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Hemscheidt, Thomas. Semi-Synthesis and In-Vitro Anticancer Evaluation of Derivatives of a New Microtubule Poison with a Taxol-Like Mechanism. Defense Technical Information Center, 2002. http://dx.doi.org/10.21236/ada411590.

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Hemscheidt, Thomas U. Semi-Synthesis and In-Vitro Anticancer Evaluation of Derivatives of a New Microtubule Poison with a Taxol-Like Mechanism. Defense Technical Information Center, 2003. http://dx.doi.org/10.21236/ada419388.

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Hemscheidt, Thomas K. Semi-Synthesis and In-vitro Anticancer Evaluation of Derivatives of a New Microtubule Poison with a Taxol-Like Mechanism. Defense Technical Information Center, 2004. http://dx.doi.org/10.21236/ada469112.

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