Paper
Organic & Biomolecular Chemistry
K. Johnston, W. C. Rose, J. F. Kadow, D. M. Vyas and
S.-H. Chen, Bioorg. Med. Chem. Lett., 2000, 10, 1327–1331;
(f) E. J. Roh, D. Kim, C. O. Lee, S. U. Choi and C. E. Song,
Bioorg. Med. Chem., 2002, 10, 3145–3151.
Notes and references
1 (a) K. C. Nicolaou, W.-M. Dai and R. K. Guy, Angew. Chem.,
Int. Ed. Engl., 1994, 33, 15–44; (b) K. C. Nicolaou and
R. K. Guy, Angew. Chem., Int. Ed. Engl., 1995, 34, 2079–2090. 14 Selected references: (a) J.-N. Denis, A. E. Greene, A. A. Serra
2 H. Oettle, Cancer Treat. Rev., 2014, 40, 1039–1047.
3 D. Lorusso, F. Petrelli, A. Coinu, F. Raspagliesi and
S. Barni, Gynecol. Oncol., 2014, 133, 117–123.
4 Q. Chu, M. Vincent, D. Logan, J. A. Mackay and
W. K. Evans, Lung Cancer, 2005, 50, 355–374.
5 V. Barsch, Das Taxol Buch, Georg Thieme Verlag, Stuttgart,
2004.
6 S. B. Horwitz, J. Fant and P. B. Schiff, Nature, 1979, 277,
665–667.
7 S. Sharma, C. Lagisetti, B. Poliks, R. M. Coates,
D. G. I. Kingston and S. Bane, Biochem., 2013, 52, 2328–
2336.
8 M. Magnani, G. Maccari, J. M. Andreu, J. F. Díaz and
M. Botta, FEBS J., 2009, 276, 2701–2712.
9 (a) R. A. Jibodh, J. S. Lagas, B. Nuijen, J. H. Beijnen and
J. H. M. Schellens, Eur. J. Pharmacol., 2013, 717, 40–46;
(b) V. A. de Weger, J. H. Beijnen and J. H. M. Schellens,
Anti-Cancer Drugs, 2014, 25, 488–494.
10 (a) J. A. Yared and K. H. R. Tkaczuk, Drug Des., Dev. Ther.,
2012, 6, 371–384; (b) I. Ojima, R. Geney, I. M. Ungureanu
and D. Li, IUBMB Life, 2002, 53, 269–274; (c) G. A. Orr,
P. Verdier-Pinard, H. McDaid and S. Band Horwitz,
Oncogene, 2003, 22, 728–7295.
and M. J. Luche, J. Org. Chem., 1986, 51, 46–50;
(b) J.-N. Denis, A. Correa and A. E. Greene, J. Org. Chem.,
1990, 55, 1957–1959; (c) L. Deng and E. N. Jacobsen, J. Org.
Chem., 1992, 57, 4320–4323; (d) Z.-M. Wang, H. C. Kolb
and K. B. Sharpless, J. Org. Chem., 1994, 59, 5104–5105;
(e) M. E. Bunnage, S. G. Davies and C. J. Goodwin, J. Chem.
Soc., Perkin Trans. 1, 1994, 2385–2391; (f) R. P. Srivastava,
J. K. Zjawiony, J. R. Peterson and J. D. McChesney, Tetra-
hedron: Asymmetry, 1994, 5, 1683–1688; (g) Enantioselective
Synthesis of β-Amino Acids, ed. E. Juaristi, Wiley-VCH, Wein-
heim, 1996; (h) S. H. Kang, C. M. Kim and J.-H. Youn, Tetra-
hedron Lett., 1999, 40, 3581–3582; (i) S.-H. Lee, J. Yoon,
K. Nakamura and Y.-S. Lee, Org. Lett., 2000, 2, 1243–1246;
( j) Z. Zhou, X. Mei, J. Chang and D. Feng, Synth. Commun.,
2001, 31, 3609–3615; (k) J. M. Andrés, M. A. Martínez,
R. Pedrosa and A. Pérez-Encabo, Tetrahedron: Asymmetry,
2001, 12, 347–253; (l) M. V. Voronkov, A. V. Gontcharov and
Z.-M. Wang, Tetrahedron Lett., 2003, 44, 407–409;
(m) Z. Zhou and X. Mei, Synth. Commun., 2003, 33, 723–
728; (n) J.-M. Lee, H.-S. Lim, K.-C. Seo and S.-K. Chung,
Tetrahedron:
Asymmetry,
2003,
14,
3639–3641;
(o) J. C. Borah, S. Gogoi, J. Boruwa, B. Kalita and
N. C. Barua, Tetrahedron Lett., 2004, 45, 3689–3691;
(p) W.-J. Liu, B.-D. Lv and L.-Z. Gong, Angew. Chem., Int.
Ed., 2009, 48, 6503–6506; (q) P. Dziedzic, P. Schyman,
M. Kullberg and A. Córdova, Chem. – Eur. J., 2009, 15,
4044–4048; (r) L. Munoz-Hernández and J. A. Soderquist,
Org. Lett., 2009, 11, 2571–2574; (s) Y. Qian, X. Xu, L. Jiang,
D. Prajapati and W. Hu, J. Org. Chem., 2010, 75, 7483–7486;
(t) J.-L. Jiang, M. Yao and C.-D. Lu, Org. Lett., 2014, 16, 318–
321.
11 Recent examples include: (a) S. Zhao, W. Wang, Y. Huang,
Y. Fu and Y. Cheng, Med. Chem. Commun., 2014, 5, 1658–
1663; (b) A. G. Cheetham, P. Zhang, Y.-A. Lin, R. Lin and
H. Cui, J. Mater. Chem. B, 2014, 2, 7316–7326;
(c) E. Bouvier, S. Thirot, F. Schmidt and C. Monneret, Org.
Biomol. Chem., 2003, 1, 3343–3352; (d) X. Hu, J. Li, W. Lin,
Y. Huang, X. Jing and Z. Xie, RSC Adv., 2014, 4, 38405–
38411; (e) M. V. Trmcic, R. V. Matovic, G. I. Tovilovic,
B. Z. Ristic, V. S. Trajkovic, Z. B. Ferjancic and R. N. Saicic, 15 (a) R. N. Patel, Annu. Rev. Microbiol., 1998, 98, 361–395;
Org. Biomol. Chem., 2012, 10, 4933–4942.
12 (a) D. G. I. Kingston, Phytochemistry, 2007, 68, 1844–1854;
(b) M. Zagozda and J. Plenkiewicz, Tetrahedron: Asymmetry,
2008, 19, 1455–1460.
(b) Y.-F. Wang, Q.-W. Shi, M. Dong, H. Kiyota, Y.-C. Gu and 16 Selected references: (a) G. Cardillo, L. Gentilucci,
B. Cong, Chem. Rev., 2011, 111, 7652–7709 and references
cited therein; (c) K. C. Nicolaou and R. A. Valiulin, Org.
Biomol. Chem., 2013, 11, 4154–4163; (d) W.-S. Fang and
X.-T. Liang, Mini-Rev. Med. Chem., 2005, 5, 1–12.
A. Tolomelli and C. Tomasini, J. Org. Chem., 1998, 63,
2351–2353; (b) G. Cardillo, A. Tolomelli and C. Tomasini,
Eur. J. Org. Chem., 1999, 155–161.
17 Selected references: (a) J. C. Borah, J. Boruwa and
N. C. Barua, Curr. Org. Synth., 2007, 4, 175–199; (b) E. Forró
and F. Fülöp, Tetrahedron: Asymmetry, 2010, 21, 637–639;
(c) R. Brieva, J. Z. Crich and C. J. Sih, J. Org. Chem., 1993,
58, 1068–1075; (d) H. Hönig, P. Seufer-Wasserthal and
13 (a) O. Expósito, M. Bonfill, E. Moyano, M. Onrubia,
M. H. Mirjalili, R. M. Cusidó and J. Palazóna, Anti-Cancer
Agents Med. Chem., 2009, 9, 109–121; (b) F. Guéritte-Voege-
lein, D. Guénard, F. Lavelle, M.-T. Le Goff, L. Mangatal and
P. Potier, J. Med. Chem., 1991, 34, 992–998; (c) C. Colderch,
Y. Tang, J. Klett, S.-E. Zhang, Y.-T. Ma, W. Shaorong,
R. Matesanz, B. Pera, A. Canales, J. Jíménez-Barbero,
A. Morreale, J. F. Díaz, W.-S. Fang and F. Gago, Org. Biomol.
Chem., 2013, 11, 3046–3056; (d) S.-H. Chen, M. Xue,
S. Huang, B. H. Long, C. A. Fairchild, W. C. Rose,
J. F. Kadow and D. Vyas, Bioorg. Med. Chem. Lett., 1997, 7,
3057–3062; (e) M. Xue, B. H. Long, C. Fairchild,
H.
Weber,
Tetrahedron,
1990,
46,
3841–3850;
(e) H. Hamamoto, V. A. Mamedov, M. Kitamoto, N. Hayashi
and S. Tsuboi, Tetrahedron: Asymmetry, 2000, 11, 4485–
4407; (f) R. N. Patel, A. Banerjee, R. Y. Ko, J. M. Howell,
W.-S. Li, F. T. Comezoglu, R. A. Partyka and L. Szarka, Bio-
technol. Appl. Biochem., 1994, 20, 23–33; (g) D.-M. Gou,
Y.-C. Liu and C.-S. Chen, J. Org. Chem., 1993, 58, 1287–
1289; (h) C. J. Shi, in Enantioselective Synthesis of β-Amino
Org. Biomol. Chem.
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