Chapter 11 Total synthesis and mechanism of action studies on the antitumor alkaloid, (-)-agelastatin a

Strategies and Tactics in Organic Synthesis

Volumn 6, Issue C, 2005, Pages 352-394

  Hale, Karl J ^a   Domostoj, Mathias M ^a   El Tanani, Mohamed ^b   Charles Campbell, F ^b   Mason, Charlene K ^b  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

^b QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 41649120463     PISSN: 18746004     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S1874-6004(05)80034-6     Document Type: Article

References (109)

1. Breinbauer R., Vetter I.R., and Waldmann H. Angew. Chem. Int. Ed. 41 (2002) 2878
2. For a leading review on the uses of ethylnitrosourea (ENU)-induced mutagenesis for genome analysis, see. Balling R. Annu. Rev. Genomics, Hum. Genet. 2 (2001) 463
3. For an excellent article on the first rats to have their breast cancer suppressor genes Brca1 and Brca2 knocked out see. Zan Y., Haag J.D., Chen K.-S., Shepel L.A., Wigington D., Wang Y.-R., Hu R., Lopez-Guajardo C.C., Brose H.L., Porter K.I., Leonard R.A., Hitt A.A., Schommer S.L., Elegbede A.F., and Gould M.N. Nat. Biotech. 21 (2003) 645
4. For some excellent reviews on RNA interference see. Dykxhoorn D.M., Novina C.D., and Sharp P.A. Nature Rev. Molecular Cell Biology 4 (2003) 457
5. Hannon G.J. Nature 418 (2002) 244
6. Brummelkamp T.R., and Bernards R. Nat. Rev. Cancer 3 (2003) 781
7. For discussions of the utility of small molecules for dissecting cell signaling pathways see. Mitchison T.J. Chem. Biol. 1 (1994) 3
8. Schreiber S.L. Biorg. Med. Chem. 6 (1998) 1127
9. Hinterding K., Alonso-Diaz D., and Waldmann H. Angew. Chem. Int. Ed. 37 (1998) 688
10. Crews C.M., and Splittgerber U. TIBS 24 (1999) 317
11. Stockwell B.R. Trends Biotechnol. 18 (2000) 449
12. Stockwell B.R. Nat. Rev. Genetics 1 (2000) 116
13. Alaimo P.J., Shogren-Knaak M.A., and Shokat K.M. Curr. Opin. Chem. Biol. 5 (2001) 360
14. Schreiber S.L. Chem. Eng. News March 3 (2003) 51
15. For examples of the use of latex microspheres in the affinity chromatographic purification of drug receptors, see. Shimizu N., Sugimoto K., Tang J., Nishi T., Sata I., Hiramoto M., Aizawa S., Hatakeyama M., Ohba R., Hatori H., Yoshikawa T., Suzuki F., Oomori A., Tanaka H., Kawaguchi H., Watanabe H., and Handa H. Nat. Biotechnol. 18 (2000) 877
16. For a recent successful example of the immobilization of the antibiotic, moenomycin A, on sepharose, and its use for the purification of the penicillin binding protein 1b (PBP 1b), see. Stembera K., Buchynskyy, Vogel S., Knoll D., Osman A.W., Ayala J.A., and Welzel P. ChemBioChem 3 (2002) 332
17. Zenkoh T., Hatori H., Tanaka H., Hasegawa M., Hatakeyama M., Kabe Y., Setoi H., Kawaguchi H., Handa H., and Takahashi T. Org. Lett. 6 (2004) 2477
18. Hatori H., Zenkoh T., Kobayashi M., Ohtsu Y., Shigematsu N., Setoi H., Hino M., and Handa H. J. Antibiotics 57 (2004) 456
19. Hale K.J., Frigerio M., Manaviazar S., Hummersone M.G., Roberts G.C.K., Fillingham I., Barsukov I., and Gescher A. Org. Lett. 5 (2003) 499
20. Ge N.-H., and Hochstrasser R.M. PhysChemComm 5 (2002) 17
21. Mittl P.R.E., and Gritter M.G. Curr. Opin. Chem. Biol. 5 (2001) 402
22. Stevens R.C. Curr. Opin. Struct. Biol. 10 (2000) 558
23. Burke M.D., and Schreiber S.L. Angew. Chem. Int. Ed. 43 (2004) 46
24. See for example. Blunt J.W., Copp B.R., Munro M.H.G., Nothcote P.T., and Prinsep M.R. Nat. Prod. Rep. 21 (2004) 1
25. Blunt J.W., Copp B.R., Munro M.H.G., Nothcote P.T., and Prinsep M.R. Nat. Prod. Rep. 20 (2003) 1
26. Faulkner D.J. Nat. Prod. Rep. 19 (2002) 1
27. Faulkner D.J. Nat. Prod. Rep. 18 (2001) 1
28. In: Hale K.J. (Ed). The Chemical Synthesis of Natural Products (2000), Blackwell, Oxford
29. Macleod K. For some reviews and papers that discuss the Wnt/APC/β-Catenin Cell Signalling Pathway, see. Curr. Opin. Gen. Dev. 10 (2000) 81
30. Watson S.A. Lancet 357 (2001) 572
31. van Noort M., and Clevers H. Dev. Biol. 244 (2002) 1
32. Polakis P. Genes Dev. 14 (2000) 1837
33. Takahashi M., Tsunoda T., Seiki M., Nakamura Y., and Furukawa Y. Oncogene 21 (2002) 5861
34. van Es J.H., Barker N., and Clevers H. Curr. Opin. Gen. Dev. 13 (2003) 28
35. He X. Dev. Cell 4 (2003) 791
36. Nelson W.J., and Nusse R. Science 303 (2004) 1483
37. Chung D.C. Gastroenterology 119 (2000) 854
38. D'Ambrosio M., Guerriero A., Debitus C., Ribes O., Pusset J., Leroy S., and Pietra F. J. Chem. Soc. Chem. Commun. (1993) 1305
39. D'Ambrosio M., Guerriero A., Chiasera G., and Pietra F. Helv. Chim. Acta 77 (1994) 1895
40. D'Ambrosio M., Guerriero A., Ripamonti M., Debitus C., Waikedre J., and Pietra F. Helv. Chim. Acta 79 (1996) 727
41. Hong T.W., Jimenez D.R., and Molinski T.F. J. Nat. Prod. 61 (1998) 158
42. Al Mourabit A., and Potier P. Eur. J. Org. Chem. (2001) 237
43. Meijer L., Thunnissen A.M., White A.W., Garnier M., Nikolic M., Tsai L.H., Walter J., Cleverley K.E., Salinas P.C., Wu Y.Z., Biernat J., Mandelkow E.-M., Kim S.-H., and Pettit G.R. Chem. Biol. 7 (2000) 51
44. For some further information on GSK-3β see. Lovestone S., Reynolds C.H., Latimer D., Davis D.R., Anderton B.H., Gallo J.-M., Hanger D., Mulot S., and Marquardt B. Curr. Biol. 4 (1994) 1077
45. Harwood A.J. Cell 105 (2001) 821
46. Ali A., Hoeflich K.P., and Woodgett J.R. Chem. Rev. 101 (2001) 2527
47. He T.C., Sparks A.B., Rago C., Hermeking H., Zawel L., da Costa L.T., Morin P.J., Vogelstein B., and Kinzler K.W. Science 281 (1998) 1509
48. Tetsu O., and McCormick F. Nature 398 (1999) 422
49. Shutman M., Zhurinsky J., Simcha I., Albanes C., D'Amico M., Pestell R., and Ben-Ze'ev A. Proc. Nat. Acad. Sci. USA 96 (1999) 5522
50. Crawford H.C., Fungleton B.M., Rudolph-Owen L.A., Goss K.J., Rubinfeld B., Polakis P., and Matrisian L.M. Oncogene 18 (1999) 2883
51. Brabletz T., Jung T., Dag S., Hlubek F., and Kirchner T. Am. J. Pathol. 155 (1999) 1033
52. Roose J., Huls G., van Beest M., Moerer P., van der Horn K., Goldschmeding R., Lotgenberg T., and Clevers H. Science 85 (1999) 1923
53. Yamada T., Takaoka A.S., Naishiro Y., Hayashi R., Maruyama K., Maesawa C., Ochiai A., and Hirohashi S. Cancer Res. 60 (2000) 4761
54. Mann B., Gelos M., Siedow A., Hanski M.L., Gratchev A., Ilyas M., Bodmer W.F., Moyer M.P., Rieken E.O., Buhr H.J., and Hanski C. Proc. Natl. Acad. Sci USA 96 (1999) 1603
55. Lei S., Dubevkovskiy A., Chakladar A., Wojtukiewicz L., and Wang T.C. J. Biol. Chem. 279 (2004) 42492
56. Koh T.J., Bukitta C.J., Fleming J.V., Dockray G.J., Varro A., and Wang T.C. J. Clin. Invest. 106 (2000) 533
57. El-Tanani M.K., Barraclough R., Wilkinson M.C., and Rudland P.S. Oncogene 20 (2001) 1793
58. He T.C., Chan T.A., Vogelstein B., and Kinzler K.W. Cell 99 (1999) 335
59. Stein D., Anderson G.T., Chase C.E., Koh Y.-h., and Weinreb S.M. J. Am. Chem. Soc. 121 (1999) 9574
60. Anderson G.T., Chase C.E., Koh Y.-h., Stein D., and Weinreb S.M. J. Org. Chem. 63 (1998) 7594
61. Sharpless K.B., and Hori T. J. Org. Chem. 41 (1976) 176
62. Bussas R., and Kresze G. Liebigs Ann. Chem. (1980) 629
63. Feldman K.S., and Saunders J.C. J. Am. Chem. Soc. 124 (2002) 9060
64. Feldman K.S., Saunders J.C., and Laci Wrobleski M. J. Org. Chem. 67 (2002) 7096
65. Feldman K.S. Arkivoc (2003) 179
66. Furrow M.E., Schaus S.E., and Jacobsen E.N. J. Org. Chem. 63 (1998) 6776
67. Baron E., O'Brien P., and Towers T.D. Tetrahedron Lett. 43 (2002) 723
68. Knight J.G., and Muldowney M.P. Synlett (1995) 949
69. Grubbs R.H., and Chang S. Tetrahedron 54 (1998) 4413
70. Furstner A. Angew. Chem. Int. Ed. Engl. 39 (2000) 3012
71. Bernet B., and Vasella A. Helv. Chim. Acta. 62 (1979) 1990
72. Bernet B., and Vasella A. Helv. Chim. Acta. 62 (1979) 2400
73. We have found that SESCl is most conveniently prepared by the following literature method. Huang J., and Widlanski T.S. Other protocols for SESCl preparation include. Tetrahedron Lett. 33 (1992) 2657
74. Weinreb S.M., Demko D.M., Lessen T.A., and Demers J.P. Tetrahedron Lett. 27 (1986) 2099
75. Weinreb S.M., Chase C.E., Wipf P., and Venkatraman S. Org. Synth. 75 (1997) 161
76. Gibbs C.F., Hough L., and Richardson A.C. Carbohydrate Res. 1 (1965) 290
77. Ali Y., Richardson A.C., Gibbs C.F., and Hough L. Carbohydrate Res. 7 (1968) 255
78. Buss D.H., Hough L., and Richardson A.C. J. Chem. Soc. (1965) 2736
79. Guthrie R.D., and Murphy D. J. Chem. Soc. (1965) 3828
80. Charon D., Montage M., Pons J.-F., Le Bray K., and Chaby R. Biorg. Med. Chem. 6 (1998) 755
81. In: Boons G.J., and Hale K.J. (Eds). Organic Synthesis with Carbohydrates (2000), Blackwell Science, Oxford 56
82. Edmonds M., and Abell A. The Wittig Reaction. In: Takeda T. (Ed). Modern Carbonyl Olefination (2004), Wiley-VCH, Weinheim 1-17 Chapter 1
83. Chapter 4. Takeda T., and Tsubouchi A. Carbonyl Olefination Utilizing Metal Carbene Complexes. In: Takeda T. (Ed). Modern Carbonyl Olefination (2004), Wiley-VCH, Weinheim 151-199
84. Takai K., Kakiuchi T., Kataoka Y., and Utimoto K. J. Org. Chem. 59 (1994) 2668
85. Blakemore P.R., Cole W.J., Kocienski P.J., and Morley A. Synlett (1998) 26
86. Blakemore P.R., Kocienski P.J., Morley A., and Muir K. J. Chem. Soc. Perkin Trans. 1 (1999) 955
87. Baudin J.B., Hareau G., Julia S.A., and Ruel O. Tetrahedron Lett. 32 (1991) 1175
88. For a leading and up-to-date review on the Julia reaction, see. Dumeunier R., and Marko I.E. The Julia Reaction. Chapter 4. In: Takeda T. (Ed). Modern Carbonyl Olefination (2004), Wiley-VCH, Weinheim 104-150
89. Kingsbury J.S., Harrity J.P.A., Bonitatebus Jr. P.J., and Hoveyda A.H. J. Am. Chem. Soc. 121 (1999) 791
90. Garber S.B., Kingsbury J.S., Gray B.L., and Hoveyda A.H. J. Am. Chem. Soc. 122 (2000) 8168
91. Ward D.E., Gai Y., and Kaller B.F. J. Org. Chem. 61 (1996) 5498
92. Campbell J.A., and Hart D.J. J. Org. Chem. 58 (1993) 2900
93. Hartung J., Hunig S., Kneuer R., Schwarz M., and Wenner H. Synthesis (1997) 1433
94. For some recent examples of the AgCN mediated amidation reaction, see. Durette P.L., Baker F., Barker P.L., Boger J., Bondy S.S., Hammond M.L., Lanza T.J., Pessolano A.A., and Caldwell C.G. Tetrahedron Lett. 31 (1990) 1237
95. Hale K.J., and Cai J. J. Chem. Soc. Chem. Comm. 2319 (1997)
96. Hale K.J., Lazarides L., and Cai J. Org. Lett. 3 (2001) 2927
97. Hale K.J., and Lazarides L. Org. Lett. 4 (2002) 1903
98. Yoakim C., Ogilvie W.W., Cameron D.R., Chabot C., Guse I., Hache B., Naud J., O'Meara J.A., Plante R., and Deziel R. J. Med. Chem. 41 (1998) 2882
99. Smith III A.B., Hale K.J., and McCauley Jr. J. Tetrahedron Lett. 30 (1998) 5579
100. Parsons A.F., and Pettifer R.M. Tetrahedron Lett. 38 (1996) 1667
101. Ley S.V., Norman J., Griffith W.P., and Marsden S.P. Synthesis (1994) 639
102. Stewart I.C., Bergman R.G., and Toste F.D. J. Am. Chem. Soc. 125 (2003) 8696
103. 1 rearrangement reported by Corey in the late 1960s. See. Corey E.J., Andersen N.H., Carlson R.M., Paust J., Vedejs E., Vlattas I., and Winter R.E.K. J. Am. Chem. Soc. 90 (1968) 3245
104. Chapter 6. Newton R.F., and Roberts S.M. In: Roberts S.M., and Newton R.F. (Eds). Prostaglandins and Thromboxanes (1982), Butterworths 84
105. El-Tanani M., Barraclough R., Wilkins M.C., and Rudland P.S. Cancer Res. 61 (2001) 5619-5629
106. Oates A.J., Barraclough R., and Rudland P.S. Oncogene 13 (1996) 97-104
107. El-Tanani, M., Mason, C.K., Campbell, F.C., Domostoj, M.M., Hale, K.J. Unpublished Results
108. For the preliminary communications on our total synthesis of (-)-agelastatin A, see. Hale K.J., Domostoj M.M., Tocher D.A., Irving E., and Scheinmann F. Org. Lett. 5 (2003) 2927
109. Domostoj M.M., Irving E., Scheinmann F., and Hale K.J. Org. Lett. 6 (2004) 2615