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Synthesis of 13-epi-Taxol via a Transannular Delivery of a Borohydride Reagent

Cite this: J. Org. Chem. 1995, 60, 9, 2918–2921
Publication Date (Print):May 1, 1995
https://doi.org/10.1021/jo00114a052
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    Cited By

    This article is cited by 19 publications.

    1. Shu-Hui Chen,, Vittorio Farina,, Dolatrai M. Vyas, and, Terrence W. Doyle, , Byron H. Long and, Craig Fairchild. Synthesis and Biological Evaluation of C-13 Amide-Linked Paclitaxel (Taxol) Analogs. The Journal of Organic Chemistry 1996, 61 (6) , 2065-2070. https://doi.org/10.1021/jo952067o
    2. . References. 2009, 325-361. https://doi.org/10.1002/9783527627622.refs
    3. Pei-Pei Dong, Guang-Bo Ge, Yan-Yan Zhang, Chun-Zhi Ai, Guo-Hui Li, Liang-Liang Zhu, Hong-Wei Luan, Xing-Bao Liu, Ling Yang. Quantitative structure-retention relationship studies for taxanes including epimers and isomeric metabolites in ultra fast liquid chromatography. Journal of Chromatography A 2009, 1216 (42) , 7055-7062. https://doi.org/10.1016/j.chroma.2009.08.079
    4. Robert M. Long, Chandraiah Lagisetti, Robert M. Coates, Rodney B. Croteau. Specificity of the N-benzoyl transferase responsible for the last step of Taxol biosynthesis. Archives of Biochemistry and Biophysics 2008, 477 (2) , 384-389. https://doi.org/10.1016/j.abb.2008.06.021
    5. Meng Zhang, Dali Yin, Ji-Yu Guo, Xiao-Tian Liang. Synthesis of 7,9-dideoxybaccatin IV analogs from sinenxan A. Tetrahedron 2005, 61 (23) , 5519-5527. https://doi.org/10.1016/j.tet.2005.03.137
    6. Vaishali Deka, Joëlle Dubois, Sylviane Thoret, Françoise Guéritte, Daniel Guénard. Deletion of the Oxetane Ring in Docetaxel Analogues:  Synthesis and Biological Evaluation. Organic Letters 2003, 5 (26) , 5031-5034. https://doi.org/10.1021/ol036043c
    7. Mohd N Islam, Yuqing Song, Magdy N Iskander. Investigation of structural requirements of anticancer activity at the paclitaxel/tubulin binding site using CoMFA and CoMSIA. Journal of Molecular Graphics and Modelling 2003, 21 (4) , 263-272. https://doi.org/10.1016/S1093-3263(02)00162-6
    8. Meng Zhang, Dali Yin, Ji-Yu Guo, Xiao-Tian Liang. Synthetic study of 1,7,9-trideoxypaclitaxel via sinenxan A. Tetrahedron Letters 2002, 43 (51) , 9425-9428. https://doi.org/10.1016/S0040-4039(02)02330-4
    9. Yu Mi Ahn, David G. Vander Velde, Gunda I. Georg. Synthetic Studies with 13-Deoxybaccatin III. The Journal of Organic Chemistry 2002, 67 (20) , 7140-7143. https://doi.org/10.1021/jo011183q
    10. D. G. I. Kingston, P. G. Jagtap, H. Yuan, L. Samala. The Chemistry of Taxol and Related Taxoids. 2002, 53-225. https://doi.org/10.1007/978-3-7091-6160-9_2
    11. Luciano Barboni, Apurba Datta, Dinah Dutta, Gunda I. Georg, David G. Vander Velde, Richard H. Himes, Minmin Wang, James P. Snyder. Novel D-Seco Paclitaxel Analogues:  Synthesis, Biological Evaluation, and Model Testing. The Journal of Organic Chemistry 2001, 66 (10) , 3321-3329. https://doi.org/10.1021/jo0015467
    12. Lolita O. Zamir, Junzeng Zhang, JianHui Wu, Francoise Sauriol, Orval Mamer. Novel taxanes from the needles of Taxus canadensis. Tetrahedron 1999, 55 (50) , 14323-14340. https://doi.org/10.1016/S0040-4020(99)00930-8
    13. Lolita O. Zamir, Junzeng Zhang, Jianhui Wu, Françoise Sauriol, Orval Mamer. Five Novel Taxanes from Taxus canadensis. Journal of Natural Products 1999, 62 (9) , 1268-1273. https://doi.org/10.1021/np990160s
    14. Gunda I. Georg, Geraldine C. B. Harriman, Apurba Datta, Syed Ali, Zacharia Cheruvallath, Dinah Dutta, David G. Vander Velde, Richard H. Himes. The Chemistry of the Taxane Diterpene:  Stereoselective Reductions of Taxanes. The Journal of Organic Chemistry 1998, 63 (24) , 8926-8934. https://doi.org/10.1021/jo981194s
    15. Cesare Gennari, Michela Carcano, Monica Donghi, Nicola Mongelli, Ermes Vanotti, Anna Vulpetti. Taxol Semisynthesis:  A Highly Enantio- and Diastereoselective Synthesis of the Side Chain and a New Method for Ester Formation at C-13 Using Thioesters. The Journal of Organic Chemistry 1997, 62 (14) , 4746-4755. https://doi.org/10.1021/jo9703212
    16. Morris J. Robins, Sanchita Sarker, Vicente Samano, Stanislaw F. Wnuk. Nucleic Acid Related Compounds. 94. Remarkably High Stereoselective Reductions of 2′- and 3′-Ketonucleoside Derivatives To Give Arabino, Ribo, and Xylofuranosyl Nucleosides with Hydrogen Isotopes at C2′ and C3′. Tetrahedron 1997, 53 (2) , 447-456. https://doi.org/10.1016/S0040-4020(96)01035-6
    17. James R. Hanson. Diterpenoids. Natural Product Reports 1997, 14 (3) , 245. https://doi.org/10.1039/np9971400245
    18. Peter H. G. Wiegerinck, Lizette Fluks, Jeannet B. Hammink, Suzanne J. E. Mulders, Franciscus M. H. de Groot, Hendrik L. M. van Rozendaal, Hans W. Scheeren. Semisynthesis of Some 7-Deoxypaclitaxel Analogs from Taxine B. The Journal of Organic Chemistry 1996, 61 (20) , 7092-7100. https://doi.org/10.1021/jo960438a
    19. Mahendra D. Chordia, Milind M. Gharpure, David G.I. Kingston. Facile AB ring cleavage reactions of taxoids. Tetrahedron 1995, 51 (47) , 12963-12970. https://doi.org/10.1016/0040-4020(95)00823-Q

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