The synthesis of azadirachtin: A potent insect antifeedant

Chemistry - A European Journal

Volumn 14, Issue 34, 2008, Pages 10683-10704

  Ley, Steven V ^a   Abad Somovilla, Antonio ^b   Anderson, James C ^b   Ayats, Carles ^a   Bänteli, Rolf ^a   Beckmann, Edith ^a   Boyer, Alistair ^a   Brasca, Maria G ^b   Brice, Abigail ^a   Broughton, Howard B ^b   Burke, Brenda J ^a   Cleator, Ed ^a   Craig, Donald ^b   Denholm, Alastair A ^a   Denton, Ross M ^a   Durand Reville, Thomas ^a   Gobbi, Luca B ^a   Göbel, Michael ^a   Gray, Brian Lawrence ^a   Grossmann, Robert B ^a   Gutteridge, Claire E ^a   Hahn, Norbert ^a   Harding, Sarah L ^a   Jennens, David C ^a   Jennens, Lynn ^a   Lovell, Peter J ^b   Lovell, Helen J ^a   De La Puente, Mary L ^a   Kolb, Hartmuth C ^b   Koot, Win Jan ^a   Maslen, Sarah L ^a   McCusker, Catherine F ^a   Mattes, Amos ^a   Pape, Andrew R ^a   Pinto, Andrea ^a   Santafianos, Dinos ^b   Scott, James S ^a   Smith, Stephen C ^b   Somers, Andrew Q ^a   Spilling, Christopher D ^a   Stelzer, Frank ^a   Toogood, Peter L ^b   Turner, Richard M ^a   Veitch, Gemma E ^a   Wood, Anthony ^b   Zumbrunn, Cornelia ^a   more..

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

Azadirachtin; Claisen rearrangement; Epoxidation; Natural products; Total synthesis

Indexed keywords

HYDROCARBONS; KETONES; ORGANIC COMPOUNDS;

ALKYLATION REACTIONS; AZADIRACHTIN; BICYCLIC SYSTEMS; CARBONCARBON BONDS; CLAISEN REARRANGEMENT; CLAISEN REARRANGEMENTS; CONVERGENT APPROACHES; DECALIN; NATURAL PRODUCTS; RADICAL CYCLISATION; STEREOSELECTIVE; SYNTHESIS OF; TOTAL SYNTHESIS;

ETHERS;

AZADIRACHTIN; INSECTICIDE; LIMONOID;

ARTICLE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS;

INSECTICIDES; LIMONINS; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 56749155796     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801103     Document Type: Article

References (98)

1. J. H. Butlerworth, E. D. Morgan. Chem. Commun. 1968, 23-24.
2. W. M. Blaney, M. S. J. Simmonds, S. V. Ley, J. C. Anderson, P. L. Toogood, Entomol. Exp. Appl. 1990, 55, 149-160.
3. M. S. J. Simmonds, W. M. Blaney, S. V. Ley, J. C. Anderson, P. L. Toogood, Entomol. Exp. Appl. 1990, 55, 169-181.
4. M. S. J. Simmonds, W. M. Blaney, R. B. Grossman, S. V. Ley, J. Insect Physiol. 1995, 41, 555-564.
5. M. S. J. Simmonds, W. M. Blaney, S. V. Ley, J. C. Anderson, R. Bänteli, A. A. Denholm, P. C. W. Green, R. B. Grossman, C. Gulleridge, L. Jennens, S. C. Smith, P. L. Toogood, A. Wood. Entomol. Exp. Appl. 1995, 77, 69-80.
6. A. J. Nisbet, A. J. Mordue, L. M. Williams, L. Hannah, L. Jennens, S. V. Ley, W. Mordue, Tissue Cell 1996, 28, 725-729.
7. A. J. Mordue Luntz, A. J. Nisbet, L. Jennens, S. V. Ley, W. Mordue, A. Juss. Int. Neem Conference, Gatton (Australia), 1996, Chapter 22.
8. A. J. Nisbet, A. J. Mordue Luntz, R. B. Grossman, L. Jennens, S. V. Ley, W. Mordue, Arch. Insect Biochem. Physiol. 1997, 34, 461-473.
9. A. J. Mordue Luntz, M. S. J. Simmonds, S. V. Ley, W. M. Blaney, W. Mordue, M. Nasiruddin, A. J. Nisbet, Pestic. Sci. 1998, 277-284.
10. A. Salehzadeh, A. Jabbar, L. Jennens, S. V. Ley, R. S. Annadurai, R. Adams, R. H. C. Strang, Pest. Manag. Sci. 2002, 58, 268-276.
11. S. L. Robertson, W. Ni, T. S. Dhadialla, A. J. Nisbet, C. McCusker, S. V. Ley, W. Mordue, A. J. Mordue-Luntz, Arch. Insect Biochem. Physiol. 2007, 64, 200-208.
12. A. J. Mordue, A. Blackwell, J. Insect Physiol. 1993, 39, 903-924.
13. H. B. Broughlon, S. V. Ley, A. M. Z. Slawin, D. J. Williams, E. D. Morgan, J. Chem. Soc. Chem. Commun. 1986, 46-47.
14. J. N. Bilton, H. B. Broughlon, P. S. Jones, S. V. Ley, Z. Liderl, E. D. Morgan, H. S. Rzepa, R. N. Sheppard, A. M. Z. Slawin, D. J. Williams, Tetrahedron 1987, 43, 2805-2815.
15. W. Kraus, M. Bokel, A. Klenk, H. Poehnl. Tetrahedron Lett. 1985, 26, 6435-6438.
16. C. J. Turner, M. S. Tempesta, R. B. Taylor, M. G. Zagorski, J. S. Termini, D. R. Schroeder, K. Nakanishi, Tetrahedron 1987, 43, 2789-2803.
17. W. Kraus, M. Bokel, A. Bruhn, R. Cramer, I. Klaiber, A. Klenk, G. Nagl, H. Poehnl, H. Sadlo, B. Volger, Tetrahedron 1987, 43, 2817-2830.
18. T. R. Govindachari, G. Gopalakrishnan, R. Raghunathan, S. S. Rajan, Curr. Sci. 1994, 66, 295-297.
19. S. V. Ley, N. S. Simpkins, A. J. Whittle, J. Chem. Soc. Chem. Commun. 1983, 503-505.
20. D. M. Hollinshead, S. C. Howell, S. V. Ley, M. Mahon, N. M. Ratcliffe, P. A. Worthington, J. Chem. Soc. Perkin Trans. 1 1983, 1579-1589.
21. A. T. Merritt, S. V. Ley, Nat. Prod. Rep. 1992, 9, 243-287.
22. S. V. Ley, D. Santafianos, W. M. Blaney, M. S. J. Simmonds, Tetrahedron Lett. 1987, 28, 221-224.
23. Y. Nishikimi, T. Iimori, M. Sodeoka, M. Shibasaki, J. Org. Chem. 1989, 54, 3354-3359.
24. J. Jauch, V. Schurig, Tetrahedron Lett. 1991, 32, 4687-4690.
25. X. T. Chen, Y. L. Luo, O. B. Zhu, Z. Wang, Chin. Chem. Lett. 1992, 3, 971-973.
26. K. J. Henry, B. Fraser-Reid, J. Org. Chem. 1994, 59, 5128-5129.
27. N. Kanoh, J. Ishihara, A. Murai, Synlett 1995, 895-897.
28. H. Watanabe, T. Watanabe, K. Mori, Tetrahedron 1996, 52, 13939-13950.
29. H. Watanabe, T. Watanabe, K. Mori, T. Kitihara, Tetrahedron Lett. 1997, 38, 4429-4432.
30. H. Schlesiger, E. Winterfeldt, Chirality 1997, 9, 454-458.
31. N. Kanoh, J. Ishihara, A. Murai, Synlett 1997, 737-739.
32. D. Haag, X. T. Chen, B. Fraser-Reid, Chem. Commun. 1998, 2577-2578.
33. a) J. Ishihara, T. Fukuzaki, A. Murai, Tetrahedron Lett. 1999, 40, 1907-1910;
34. b) J. Ishihara, Y. Yamamoto, N. Kanoh, A. Murai, Tetrahedron Lett. 1999, 40, 4387-4390.
35. D. Pflieger, B. Muckensturm, P. C. Robert, M. T. Simonis, J. C. Kienlen, Tetrahedron Lett. 1987, 28, 1519-1522
36. B. Fraser-Reid, X. T. Chen,. D. Haag, K. J. Henry, A. T. McPhail, Chirality 2000, 12, 488-495.
37. Y. Yamamoto, J. Ishihara, N. Kanoh, A. Murai, Synthesis 2000, 1894-1966.
38. K. C. Nicolaou, M. Follmann, A. J. Roecker, K. W. Hunt. Angew. Chem. 2002, 114, 2207-2210:
39. Angew. Chem. Int. Ed. 2002, 41, 2103-2106.
40. K. C. Nicolaou, A. J. Roecker, M. Follmann, R. Baati, Angew. Chem. 2002, 114, 2211-2214;
41. Angew. Chem. Int. Ed. 2002, 41, 2107-2110.
42. T. Fukuzaki, T. Kobayashi, T. Hibi, Y. Ikuma, J. Ishihara, N. Kanoh, A. Murai, Org. Lett. 2002, 4, 2877-2880.
43. K. C. Nicolaou, A. J. Roecker, H. Monenschein, P. Gunlupalli, M. Follmann, Angew. Chem. 2003, 115, 3765-3770;
44. Angew. Chem. Int. Ed. 2003, 42, 3637-3642.
45. J. Ishihara, Y. Ikuma, S. Hatakeyama, T. Suzuki, A. Murai, Tetrahedron 2003, 59, 10287-10294.
46. A. Murai, J. Toxicol. Toxin Rev. 2003, 22, 617-632.
47. S. Raina, B. A. Bhanu Prasad, V. K. Singh, Arkivoc 2003, 16-24.
48. K. C. Nicolaou, P. K. Sasmal, A. J. Roecker, X. W. Sun, S. Mandal, A. Converso. Angew. Chem. 2005, 117, 3509-3513;
49. Angew. Chem. Int. Ed. 2005, 44, 3443-3447.
50. K. C. Nicolaou, P. K. Sasmal, T. V. Kostis, A. Converso, E. Loizidou, F. Kaiser, A. J. Roecker, C. C. Dellios, X. W. Sun, G. Petrovic, Angew. Chem. 2005, 117, 3513-3518;
51. Angew. Chem. Int. Ed. 2005, 44, 3447-3452.
52. H. Watanabe, N. Mori, D. Itoh, T. Kitahara, K. Mori. Angew. Chem. 2007, 119, 1534-1538;
53. Angew. Chem. Int. Ed. 2007, 46, 1512-1516
54. S. V. Ley, J. C. Anderson, W. M. Blaney, E. D. Morgan, R. N. Sheppard, M. S. J. Simmonds, A. M. Z. Slawin, S. C. Smith, D. J. Williams, A. Wood, Tetrahedron 1991, 47, 9231-9246.
55. S. V. Ley, J. C. Anderson, W. M. Blaney, P. S. Jones, Z. Lidert, E. D. Morgan, N. G. Robinson, D. Santafianos, M. S. J. Simmonds, P. L. Toogood. Tetrahedron 1989, 45, 5175-5192.
56. H. C. Kolb, S. V. Ley, Tetrahedron Lett. 1991, 32, 6187-6190.
57. H. C. Kolb, S. V. Ley, A. M. Z. Slawin, D. J. Williams, J. Chem. Soc. Perkin Trans. 1 1992, 2735-2762.
58. W.-J. Koot, S. V. Ley, Tetrahedron 1995, 51, 2077-2090.
59. H. C. Brown, J. Am. Chem. Soc. 1966, 88, 1447-1452.
60. S. V. Ley, P. J. Lovell, A. M. Z. Slawin, S. C. Smith, D. J. Williams, A. Wood, Tetrahedron 1993, 49, 1675-1700.
61. S. V. Ley, Pure Appl. Chem. 1994, 66, 2099-2102.
62. J. C. Anderson, S. V. Ley, D. Santafianos, R. N. Sheppard, Tetrahedron 1991, 47, 6813-6850.
63. P. J. Lovell. PhD Thesis, University of London (UK). 1992.
64. H. Lovell, PhD Thesis. University of Cambridge (UK), 1994.
65. R. Bänteli, PostDoctoral Research Report, University of Cambridge (UK), 1994.
66. C. E. Gutteridge, PhD Thesis, University of Cambridge (UK), 1996.
67. For a review see: G. E. Veitch, A. Boyer, S. V. Ley, Angew. Chem. 2008, 120, 9542-9570:
68. Angew. Chem. Int. Ed. 2008, 47, 9402-9429.
69. J. Christoffers, A. Baro. Quaternary Stereocenters: Challenges and Solutions for Organic Synthesis, Wiley-VCH, Weinheim, 2006.
70. 2NEt): for full details see Supporting Information.
71. S. V. Ley, C. E. Gutteridge, A. R. Pape, C. D. Spilling, C. Zumbrunn, Synlett 1999, 1295-1297.
72. A. Q. Somers, PhD Thesis. University of Cambridge (UK), 2001.
73. M. Hiersemann, U. Nubbemeyer, The Claisen Rearrangement, Wiley-VCH, Weinheim, 2007.
74. Although our previous work depicted the trielhylsilylether at the C1 position in compound 36 (see reference [67]), further NMR studies indicated that this assignment was incorrect. It is now clear that the silyl protecting group is attached to the C3 hydroxyl group.
75. T. Durand-Reville, L. B. Gobbi, B. L. Gray, S. V. Ley, J. S. Scott, Org. Lett. 2002, 4, 3847-3850.
76. S.V. Ley, Pure Appl. Chem. 2005, 77, 1115-1130.
77. M. H. Clausen, M. R. Jorgensen, J. Thorsen, R. Madsen, J. Chem. Soc. Perkin Trans. 1 2001, 543-551.
78. S. David, S. Hanessian, Tetrahedron 1985, 41, 643-663.
79. E. Cleator, C. F. McCusker, F. Stelzer, S. V. Ley, Tetrahedron Lett. 2004, 45, 3077-3080.
80. B. Fraser-Reid, U. E. Udodong, Z. Wu, H. Ottosson, J. R. Merritt, S. M. Rao, C. Roberts, R. Madsen, Synlett 1992, 927-942.
81. L. C. Swallen, C. E. Boord, J. Am. Chem. Soc. 1930, 52, 651-660.
82. C. G. Schmitt, C. E. Boord, J. Am. Chem. Soc. 1931, 53, 2427-2428.
83. S. V. Ley, J. Norman, W. P. Griffith, S. P. Marsden, Synthesis 1994, 639-666.
84. D. H. R. Barton, S. W. McCombie, J. Chem. Soc. Perkin Trans. 1 1975, 1574-1581.
85. a) S. Ohira, Synth. Commun. 1989, 19, 561-564;
86. b) G. J. Roth, B. Liepold, S. G. Müller, H. J. Bestmann, Synlett 1996, 521-522.
87. A. N. Rai, A. Basu, Tetrahedron Lett. 2003, 44, 2267-2269.
88. G. E. Veitch, E. Beckmann, B. J. Burke, A. Boyer, S. L. Maslen, S. V. Ley, Angew. Chem. 2007, 119, 7773-7776;
89. Angew. Chem. Int. Ed. 2007, 46, 7629-7632.
90. B. D. Sherry, F. D. Toste, J. Am. Chem. Soc. 2004, 126, 15978-15979.
91. A. K. Yudin, Aziridines and Epoxides in Organic Synthesis, Wiley-VCH, Weinheim, 2006.
92. P. Brougham, M. S. Cooper, D. A. Cummerson, H. Heaney, N. Thompson. Synthesis 1987, 1015-1017.
93. G. E. Veitch, E. Beckmann, B. J. Burke, A. Boyer, C. Ayats, S. V. Ley. Angew. Chem. 2007, 119, 7777-7779;
94. Angew. Chem. Int. Ed. 2007, 46, 7633-7635.
95. M. Ball, S. P. Andrews, F. Wierschem, E. Cleator, M. Smith, S. V. Ley, Org. Lett. 2007, 9, 663-666.
96. J. L. Luche, J. Am. Chem. Soc. 1978, 100, 2226-2227.
97. A. A. Denholm, L. Jennens, S. V. Ley, A. Wood, Tetrahedron 1995, 51, 6591-6604.
98. G. E. Veitch, A. Pinto, A. Boyer, E. Beckmann, J. C. Anderson, S. V. Ley, Org. Lett. 2008, 10, 569-572.