The total synthesis of the annonaceous acetogenin 10-hydroxyasimicin

Angewandte Chemie - International Edition

Volumn 44, Issue 4, 2005, Pages 580-584

  Nattrass, Gillian L ^a   Díez, Elena ^a   McLachlan, Matthew M ^a   Dixon, Darren J ^a   Ley, Steven V ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

Metathesis; Natural products; Templating effect; Total synthesis

Indexed keywords

SYNTHESIS (CHEMICAL);

MODULAR TEMPLATING; ORTHOGONAL TEMPLATING;

ORGANIC COMPOUNDS;

10 HYDROXYASIMICIN; 2,3 BUTANEDIACETAL; ACETAL DERIVATIVE; ACETOGENIN; ASIMICIN; BUTENOLIDE; TARTARIC ACID; UNCLASSIFIED DRUG;

ANNONACEAE; ARTICLE; DIASTEREOISOMER; DIELS ALDER REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY;

ANNONACEAE; FURANS; STEREOISOMERISM;

EID: 13244249741     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200462264     Document Type: Article

References (103)

1. a) F. Q. Alali, X.-X. Liu, J. L. McLaughlin, J. Nat. Prod. 1999, 62, 504;
2. b) N. H. Oberlies, V. L. Croy, M. L. Harrison, J. L. McLaughlin, Cancer Lett. 1997, 15, 73;
3. L. Zeng, Q. Ye, N. H. Oberlies, G. Shi, Z. Gu, K. He, J. L. McLaughlin, Nat. Prod. Rep. 1996, 13, 275, and references therein.
4. For recent reviews, see: a) G. Cassiraghi, F. Zanardi, L. Battistini, G. Rassu, G. Appendino, Chemtracts: Org. Chem. 1998, 11, 803;
5. b) J. A. Marshall, K. W. Hinkle, C. E. Hagedorn, Isr. J. Chem. 1997, 37, 97;
6. R. Hoppe, H. D. Scharf, Synthesis 1995, 1447;
7. B. Figadère, Acc. Chem. Res. 1995, 28, 359, and references therein.
8. For syntheses from 1998, see: a) P. Neogi, T. Doundoulakis, A. Yazbak, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 11279;
9. b) S. C. Sinha, A. Sinha, E. Keinan, J. Am. Chem. Soc. 1598, 120, 4017;
10. S. Sasaki, K. Maruta, H. Naito, R. Maemura, E. Kawahara, M. Maeda, Chem. Pharm. Bull. 1998, 46, 154;
11. J. A. Marshall, H. J. Jiang, J. Org. Chem. 1998, 63, 7066;
12. e) A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863;
13. f) S. E. Schaus, J. Branalt, E. N. Jacobsen, J. Org. Chem. 1998, 63, 4876;
14. g) S. Hanessian, T. A. Grillo, J. Org. Chem. 1998, 63, 1049;
15. h) H. Makabe, A. Tanaka, T. Oritani, Tetrahedron 1998, 54, 6329;
16. J. A. Marshall, H. J. Jiang, Tetrahedron Lett. 1998, 39, 1493;
17. j) J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303.
18. For syntheses from 1999, see: a) S. Bäurle, S. Hoppen, U. Koert, Angew. Chem. 1999, 111, 1341; Angew. Chem. Int. Ed. 1999, 38, 1263;
19. For syntheses from 1999, see: a) S. Bäurle, S. Hoppen, U. Koert, Angew. Chem. 1999, 111, 1341; Angew. Chem. Int. Ed. 1999, 38, 1263;
20. b) W. Kuruyama, K. Ishigami, T. Kitahara, Heterocycles 1999, 50, 981;
21. J. A. Marshall, H. J. Jiang, J. Nat. Prod. 1999, 62, 1123;
22. S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 7067;
23. e) Q. Yu, Z. J. Yao, X. G. Chen, Y. L. Wu, J. Org. Chem. 1999, 64, 2440;
24. f) A. Sinha, S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 2381;
25. g) J. A. Marshall, H. J. Jiang, J. Org. Chem. 1999, 64, 971;
26. h) S. Takahashi, K. Maeda, S. Hirota, T. Nakata, Org. Lett. 1999, 1, 2025;
27. T. S. Hu, Q. Lin, Y. L. Wu, Y. K. Wu, Org. Lett. 1999, 1, 399;
28. j) Q. Yu, Y. K. Wu, H. Ding, Y. L. Wu, J. Chem. Soc. Perkin Trans. 1 1999, 1183;
29. k) Z. M. Wang, S. K. Tian, M. Shi, Tetrahedron: Asymmetry 1999, 10, 667;
30. W. Q. Yang, T. Kitahara, Tetrahedron Lett. 1999, 40, 7827;
31. U. Emde, U. Koert, Tetrahedron Lett. 1999, 40, 5979;
32. n) Z. M. Wang, S. K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977;
33. o) S. Takahashi, T. Nakata, Tetrahedron Lett. 1999, 40, 727;
34. p) Z. M. Ruan, D. R. Mootoo, Tetrahedron Lett. 1999, 40, 49.
35. For syntheses from 2000, see: a) S. Hoppen, S. Bäurle, U. Koert, Chem. Eur. J. 2000, 6, 2382;
36. b) S. Bäurle, U. Peters, T. Friedrich, U. Koert, Eur. J. Org. Chem. 2000, 2207;
37. U. Emde, U. Koert, Eur. J. Org. Chem. 2000,1889;
38. Z. M. Wang, S. K. Tian, M. Shi, Eur. J. Org. Chem. 2000, 349;
39. e) Z. M. Wang, S. K. Tian, M. Shi, Chirality 2000,12, 581;
40. f) M. Szlosek, J. F. Peyrat, C. Chaboche, X. Franck, R. Hocquemiller, B. Figadère, New J. Chem. 2000, 24, 337;
41. g) W Q. Yang, T. Kitahara, Tetrahedron 2000, 56, 1451;
42. h) T.-S. Hu, Y-L. Wu, Y. Wu, Org. Lett. 2000, 2, 887.
43. For syntheses from 2001, see: a) C. Harken, R. Bruckner, New J. Chem. 2001, 25, 40;
44. b) T.-S. Hu, Q. Yu, Y.-L. Wu, Y. Wu, J. Org. Chem. 2001, 66, 853;
45. N. Maezaki, N. Kojima, A. Sakamoto, C. Iwata, T. Tanaka, Org. Lett. 2001, 3, 429;
46. S. D. Burke, L. Jiang, Org. Lett. 2001, 3, 1953.
47. For syntheses from 2002, see: a) S. Takahashi, A. Kubota, T. Nakata, Angew. Chem. 2002, 114, 4945; Angew. Chem. Int. Ed. 2002, 41, 4751;
48. For syntheses from 2002, see: a) S. Takahashi, A. Kubota, T. Nakata, Angew. Chem. 2002, 114, 4945; Angew. Chem. Int. Ed. 2002, 41, 4751;
49. b) S. Takahashi, T. Nakata, J. Org. Chem. 2002, 67, 5739;
50. S. Jiang, Z.-H. Liu, G. Sheng, B.-B. Zeng, X.-G. Cheng, Y.-L. Wu, Z.-J. Yao, J. Org. Chem. 2002, 67, 3404;
51. A. R. L. Cecil, R. C. D. Brown, Org. Lett. 2002, 4, 3715;
52. e) H. Makabe, Y. Hattori, A. Tanoka, T. Oritani, Org. Lett. 2002, 4, 1083;
53. f) E. Keinan, S. C. Sinha, Pure Appl. Chem. 2002, 74, 93;
54. g) S. Takahashi, A. Kubota, T. Nakata, Tetrahedron Lett. 2002, 43, 8661.
55. For syntheses from 2003, see: a) N. Maezaki, N. Kojima, A. Sakamoto, H. Tominaga, C. Iwata, T. Tanaka, M. Monden, B. Damdinswen, S. Nakamori, Chem. Eur. J. 2003, 9, 390;
56. b) B.-B. Zeng, Y. Wu, S. Jiang, Q. Yu, Z.-J. Yao, Z.-H. Liu, H.-Y. Li, Y. Li, X.-G. Chen, Y.-L. Wu, Chem. Eur. J. 2003, 9, 282;
57. P. A. Evans, J. Cui, S. J. Gharpure, A. Polosukhi, H. R. Zhang, J. Am. Chem. Soc. 2003, 725, 14072;
58. J. A. Marshall, A. Piettre, M. A. Paige, F. Valeriate, J. Org. Chem. 2003, 68, 8290;
59. e) J. A. Marshall, A. Piettre, M. A. Paige, F. Valeriate, J. Org. Chem. 2003, 68, 1780;
60. f) J. A. Marshall, A. Piettre, M. A. Paige, F. Valeriate, J. Org. Chem. 2003, 68, 1771;
61. g) L. Zhu, D. R. Mootoo, Org. Lett. 2003, 5, 3475;
62. h) S. Takahashi, A. Kubota, T. Nakata, Org. Lett. 2003, 5, 1353;
63. R. V. A. Orru, B. Groenendaal, J. van Heyst, M. Hunting, C. Wesseling, R. F. Schmilz, S. F. Mayer, K. Faber, Pure Appl. Chem. 2003, 75, 259;
64. j) S. Takahashi, A. Kubota, T. Nakata, Tetrahedron 2003, 59, 1627;
65. k) J. L. Lee, C. F. Lin, L. Y. Hsieh, W. R. Lin, H. F. Chiu, Y. C. Wu, K. S. Wang, M. J. Wu, Tetrahedron Lett. 2003, 44, 7833;
66. S. R. V. Kandula, P. Kumar, Tetrahedron Lett. 2003, 44, 6149.
67. For syntheses from 2004, see: a) N. Maezaki, H. Tominaga, N. Kojima, M. Yanai, D. Urabe, T. Tanaka, Chem. Commun. 2004, 406;
68. b) H. N. Han, M. K. Sinha, L. J. D'Souza, E. Keinan, S. C. Sinha, Chem. Eur. J. 2004, 10, 2149;
69. Q. S. Zhang, H. J. Lu, C. Richard, D. P. Curran, J. Am. Chem. Soc. 2004, 126, 36;
70. A. R. Cecil, Y. L. Hu, M. J. Vicent, R. Duncan, R. C. D. Brown, J. Org. Chem. 2004, 69, 3368;
71. e) L. Zhu, D. R. Mootoo, J. Org. Chem. 2004, 69, 3154;
72. f) T. Yoshimitsu, T. Makino, H. Nagaoka, J. Org. Chem. 2004, 69, 1993;
73. g) H. Makabe, A. Miyawaki, R. Takahashi, Y. Hattori, M. Abe, H. Miyoshi. Tetrahedron Lett. 2004, 45, 973.
74. a) D. J. Dixon, S. V. Ley, D. J. Reynolds, Angew. Chem. 2000, 112, 3768; Angew. Chem. Int. Ed. 2000, 39, 3622;
75. a) D. J. Dixon, S. V. Ley, D. J. Reynolds, Angew. Chem. 2000, 112, 3768; Angew. Chem. Int. Ed. 2000, 39, 3622;
76. b) D. J. Dixon, S. V. Ley, D. J. Reynolds, Chem. Eur. J. 2002, 8, 1621.
77. K. He, G. Shi, G.-X. Zhao, L. Zeng, Q. Ye, J. T. Schwedler, K. V. Wood, J. L. McLaughlin, J. Nat. Prod. 1996, 59, 1029.
78. S. V. Ley, D. K. Baeschlin, D. J. Dixon, A. C. Foster, S. J. Ince, H. W. M. Priepke, D. J. Reynolds. Chem. Rev. 2001, 101, 53; and references therein.
79. a) Y. Sakamoto, M. Okazaki, K. Miyamoto, T. Nakata, Tetrahedron Lett. 2001, 42, 7633;
80. b) E. C. Hansen, D. Lee, J. Am. Chem. Soc. 2003, 125, 9582;
81. P. A. Evans, J. Cui, G. P. Buffone, Angew. Chem. 2003, 115, 1776-1779; Angew. Chem. Int. Ed. 2003, 42, 1734, and references therein.
82. P. A. Evans, J. Cui, G. P. Buffone, Angew. Chem. 2003, 115, 1776-1779; Angew. Chem. Int. Ed. 2003, 42, 1734, and references therein.
83. a) J. Mulzer, K. Schein, J. W. Bats, J. Buschmann, P. Luger, Angew. Chem. 1998, 110, 1625; Angew. Chem. Int. Ed. 1998, 37, 1566;
84. a) J. Mulzer, K. Schein, J. W. Bats, J. Buschmann, P. Luger, Angew. Chem. 1998, 110, 1625; Angew. Chem. Int. Ed. 1998, 37, 1566;
85. b) J. Mulzer, I. Böhm, J. W. Bats, Tetrahedron Lett. 1998, 39, 9643.
86. In this particular synthesis, the two alkenol units are the same, but any absolute configurational arrangement can, in principle, be loaded onto the orthogonal 4-bromomethylbenzyl chloride template by making use of the greater reactivity of the acyl chloride relative to the alkyl bromide substituent.
87. A noticeable improvement in stereocontrol was observed in going from ortho to meta and finally to para substitution. The results of these investigations will be published in a full paper at a later date.
88. M. Scholl, S. Ding, C. W. Lee, R. H. Grubbs, Org. Lett. 1999, 1, 953.
89. Comparable diastereoselectivity was obtained in the Sharpless asymmetric dihydroxylation reaction when performed on the open chain hydroxy ester, obtained from the transesterfiction reaction on the alkene formed immediately after the RCM reaction.
90. Orthogonal macrocycle opening was achieved under transfer-hydrogenation conditions and will be communicated in a full paper at a later date.
91. a) D. B. Dess, J. C. Martin, J. Org. Chem. 1983, 48, 4155;
92. b) D. B. Dess, J. C. Martin, J. Am. Chem. Soc. 1991, 113, 7277.
93. J. M. Williams, R. B. Jobson, N. Yasuda, G. Marchesini, U.-H. Dolling, E. J. J. Grabowski, Tetrahedron Lett. 1595, 36, 5461.
94. M. Muller, A. Mann, M. Taddei, Tetrahedron Lett. 1993, 34, 3289.
95. E. J. Corey, R. K. Bakshi, S. J. Shibata, J. Am. Chem. Soc. 1987, 709, 5551.
96. Investigations into using alternative nitrosodienophiles to improve the regioselectivity of the desired HDA reaction indicated that nitrosobenzene gives the most favorable results and could not be improved on. These results will be communicated in a full paper at a later date.
97. a) M. Nitta, T. Kobayashi, J. Chem. Soc. Perkin Trans. 1 1985, 1401;
98. b) S. Cicchi, A. Goti, A. Brondi, A. Guarna, F. De Sarlo, Tetrahedron Lett. 1990, 31, 3351.
99. S. V. Ley, J. Norman, W. P. Griffith, S. P. Marsden, Synthesis 1994, 639.
100. K. Takai, K. Nitta, K. Utimoto, J. Am. Chem. Soc. 1986, 108, 7408.
101. a) T. R. Hoye, P. R. Hanson, A. C. Kovelesky, T. D. Ocain, Z. P. Zhuang, J. Am. Chem. Soc. 1991, 113, 9369;
102. b) K. Sonogashira, Y. Thoda, N. Magihara, Tetrahedron Lett. 1975, 4467.
103. +: 661.4650; found: 661.4651.