The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: The southern hemisphere EF segment

Organic and Biomolecular Chemistry

Volumn 3, Issue 13, 2005, Pages 2420-2430

  Paterson, Ian ^a   Coster, Mark J ^a,b   Chen, David Y K ^a   Aceña, José L ^a   Bach, Jordi ^a   Keown, Linda E ^a   Trieselmann, Thomas ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b UNIVERSITY OF SYDNEY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; CYTOLOGY; KETONES; MOLECULAR STRUCTURE; REACTION KINETICS; STEREOCHEMISTRY; SUBSTRATES; TOXICITY;

ALTOHYRTIN; BORON ALDOL REACTIONS; STEREOCENTERS; STEREOCONTROLLED SYNTHESIS;

SYNTHESIS (CHEMICAL);

ACETAL DERIVATIVE; ALCOHOL DERIVATIVE; ANTINEOPLASTIC AGENT; BORON; MACROLIDE; PYRAN DERIVATIVE; SPIRO COMPOUND; SPONGISTATIN 1;

CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; REVIEW; STEREOISOMERISM; SYNTHESIS; THERMODYNAMICS;

ACETALS; ALCOHOLS; ANTINEOPLASTIC AGENTS; BORON; KINETICS; MACROLIDES; MOLECULAR STRUCTURE; PYRANS; SPIRO COMPOUNDS; STEREOISOMERISM; THERMODYNAMICS;

EID: 22744456562     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b504149j     Document Type: Review

References (82)

1. For a full introduction and background, see the preceding papers in this series: I. Paterson, M. J. Coster, D. Y.-K. Chen, R. M. Oballa, D. J. Wallace and R. D. Norcross, Org. Biomol, Chem., 2005, 3, DOI: 10.1039/b504146e;
2. I. Paterson, M. J. Coster, D. Y.-K. Chen, K. R. Gibson and D. J. Wallace, Org. Biomol. Chem., 2005, 3, DOI: 10.1039/b504148a.
3. For previous communications of our work, see: (a) I. Paterson, R. M. Oballa and R. D. Norcross, Tetrahedron Lett., 1996, 37, 8581-8584;
4. (b) I. Paterson and L. E. Keown, Tetrahedron Lett., 1997, 38, 5727-5730;
5. (c) I. Paterson and R. M. Oballa, Tetrahedron Lett., 1997, 38, 8241-8244;
6. I. Paterson, D. J. Wallace and K. R. Gibson, Tetrahedron Lett., 1997, 38, 8911-8914;
7. (e) I. Paterson, D. J. Wallace and R. M. Oballa, Tetrahedron Lett., 1998, 39, 8545-8548;
8. (f) I. Paterson, D. Y.-K. Chen, M. J. Coster, J. L. Acena, J. Bach, K. R. Gibson, L. E. Keown, R. M. Oballa, T. Trieselmann, D. J. Wallace, A. P. Hodgson and R. D. Norcross, Angew. Chem., Int. Ed., 2001, 40, 4055-4060;
9. (g) I. Paterson and M. J. Coster, Tetrahedron Lett., 2002, 43, 3285-3289;
10. (H) I. Paterson, J. L. Acena, J. Bach, D. Y.-K. Chen and M. J. Coster, Chem. Commun., 2003, 462-463;
11. (i) I. Paterson and M. J. Coster, in Strategy and Tactics in Organic Synthesis, ed. M. Harmata, Elsevier, Oxford, 2004, vol. 4, ch. 8, pp. 211-245.
12. Completed altohyrtin/spongistatin total syntheses: (a) D. A. Evans, P. J. Coleman and L. C. Dias, Angew. Chem., Int. Ed., 1997, 36, 2738-2741;
13. (b) D. A. Evans, B. W. Trotter, B. Cote and P. J. Coleman, Angew. Chem., Int. Ed., 1997, 36, 2741-2744;
14. (c) D. A. Evans, B. W. Trotter, B. Cote, P. J. Coleman, L. C. Dias and A. N. Tyler, Angew. Chem., Int. Ed., 1997, 36, 2744-2747;
15. (d) D. A. Evans, B. W. Trotter, P. J. Coleman, B. Cote, L. C. Dias, H. A. Rajapakse and A. N. Tyler, Tetrahedron, 1999, 55, 8671-8726;
16. (e) J. Guo, K. J. Duffy, K. L. Stevens, P. I. Dalko, R. M. Roth, M. M. Hayward and Y. Kishi, Angew. Chem., Int. Ed., 1998, 37, 187-192;
17. (f) M. M. Hayward, R. M. Roth, K. J. Duffy, P. I. Dalko, K. L. Stevens, J. Guo and Y. Kishi, Angew. Chem., Int. Ed., 1998, 37, 192-196;
18. (g) A. B. Smith, III, V. A. Doughty, Q. Lin, L. Zhuang, M. D. McBriar, A. M. Boldi, W. H. Moser, N. Murase, K. Nakayama and M. Sobukawa, Angew. Chem., Int. Ed., 2001, 40, 191-195;
19. (h) A. B. Smith, III, Q. Lin, V. A. Doughty, L. Zhuang, M. D. McBriar, J. K. Kerns, C. S. Brook, N. Murase and K. Nakayama, Angew. Chem., Int. Ed., 2001, 40, 196-199;
20. (i) A. B. Smith, III, V. A. Doughty, C. Sfouggatakis, C. S. Bennett, J. Koyanagi and M. Takeuchi, Org. Lett., 2002, 4, 783-786;
21. (f) A. B. Smith, III, W. Zhu, S. Shirakami, C. Sfouggatakis, V. A. Doughty, C. S. Bennett and Y. Sakamoto, Org. Lett., 2003, 5, 761-764;
22. (k) M. T. Crimmin and D. G. Washburn, Tetrahedron Lett., 1998, 39, 7487-7490;
23. (l) M. T. Crimmin, J. D. Katz, L. C. McAtee, E. A. Tabet and S. J. Kirincich, Org. Lett., 2001, 3, 949-952;
24. (m) M. T. Crimmin and J. D. Katz, Org. Lett., 2000, 2, 957-960;
25. (n) M. T. Crimmin, J. D. Katz, D. G. Washburn, S. P. Allwein and L. F. McAtee, J. Am. Chem. Soc., 2002, 124, 5661-5663;
26. (o) J. L. Hubbs and C. H. Heathcock, J. Am. Chem. Soc., 2003, 125, 12836-12843;
27. (p) C. H. Heathcock, M. McLaughlin, J. Medina, J. L. Hubbs, G. A. Wallace, R. Scott, M. M. Claffey, C. J. Hayes and G. R. Ott, J. Am. Chem. Soc., 2003, 125, 12844-12849.
28. Formal total synthesis of altohyrtin C/spongistatin 2 by Nakata and co-workers: T. Terauchi, T. Terauchi, I. Sato, W. Shoji, T. Tsukada, T. Tsunoda, N. Kanoh and M. Nakata, Tetrahedron Lett., 2003, 44, 7741-7745;
29. T. Terauchi, T. Tanaka, T. Terauchi, M. Morita, K. Kimijima, I. Sato, W. Shoji, Y. Nakamura, T. Tsukada, T. Tsunoda, G. Hayashi, N. Kanoh and M. Nakata, Tetrahedron Lett., 2003, 44, 7747-7751.
30. Syntheses of E- and/or F-ring subunits by other groups: J. C. Anderson and B. P. McDermott, Tetrahedron Lett., 1999, 40, 7135-7138;
31. J. C. Anderson, B. P. McDermott and E. J. Griffin, Tetrahedron, 2000, 56, 8747-8767;
32. R. Dunkel, J. Treu, H. Martin and R. Hoffmann, Tetrahedron: Asymmetry, 1999, 10, 1539-1549;
33. H. Kim and H. M. R. Hoffmann, Eur. J. Org. Chem., 2000, 2195-2201;
34. E. Fernandez-Megia, N. Gourlaouen, S. V. Ley and G. J. Rowlands, Synlett, 1998, 991-994;
35. I. H. Cho and L. A. Paquette, Heterocycles, 2002, 58, 43-46;
36. S. A. Hermitage, S. M. Roberts and D. J. Watson, Tetrahedron Lett., 1998, 39, 3567-3570;
37. P. D. Kary, S. M. Roberts and D. J. Watson, Tetrahedron: Asymmetry, 1999, 10, 213-216;
38. P. D. Kary and S. M. Roberts, Tetrahedron: Asymmetry, 1999, 10, 217-219;
39. G. C. Micalizio and W. R. Roush, Tetrahedron Lett., 1999, 40, 3351-3354;
40. G. C. Micalizio, A. N. Pinchuk and W. R. Roush, J. Org. Chem., 2000, 65, 8730-8736;
41. M. Samadi, C. Mmioz-Letelier, S. Poigny and M. Guyot, Tetrahedron Lett., 2000, 41, 3349-3353;
42. S. Lemaire-Audoire and P. Vogel, Tetrahedron Lett., 1998, 39, 1345-1348.
43. C. J. Cowden and I. Paterson, Org. React., 1997, 51, 1-200;
44. I. Paterson, C. J. Cowden, and D. J. Wallace, in Modern Carbonyl Chemistry, ed. J. Otera, Wiley-VCH, Weinheim, 2000, pp. 249-297.
45. I. Paterson, D. J. Wallace and S. M. Velazquez, Tetrahedron Lett., 1994, 35, 9083-9086;
46. I. Paterson and D. J. Wallace, Tetrahedron Lett., 1994, 35, 9087-9090;
47. I. Paterson and D. J. Wallace, Tetrahedron Lett., 1994, 35, 9477-9480;
48. I. Paterson, D. J. Wallace and C. J. Cowden, Synthesis, 1998, 639-652
49. H. C. Brown, R. K. Dhar, K. Ganesan and B. Singaram, J. Org. Chem., 1992, 57, 499-504.
50. (a) I. Paterson and R. D. Tillyer, J. Org. Chem., 1993, 58, 4182-4184;
51. (b) I. Paterson and T.Nowak, Tetrahedron Lett., 1996, 37, 8243-8246.
52. J. A. Dale, D. L. Dull and H. S. Mosher, J. Org. Chem., 1969, 34, 2543-2549;
53. J. A. Dale and H. S. Mosher, J. Am. Chem. Soc., 1973, 95, 512-519;
54. I. Ohtani, T. Kusumi, Y. Kashman and H. Kakisawa, J. Am. Chem. Soc., 1991, 113, 4092-4096.
55. R. W. Hoffmann, Chem. Rev., 1989, 89, 1841-1860.
56. E. J. Corey, D. Barnes-Seeman and T. W. Lee, Tetrahedron Lett., 1997, 38, 4351-4354, and references cited therein.
57. D. A. Evans and K. T. Chapman, Tetrahedron Lett., 1986, 27, 5939-5942;
58. D. A. Evans, K. T. Chapman and E. M. Carreira, J. Am. Chem. Soc., 1988, 110, 3560-3578.
59. 3 reduction step: S. D. Rychnovsky and D. J. Skalitzky, Tetrahedron Lett., 1990, 31, 945-948;
60. S. D. Rychnovsky, B. Rogers and G. Yang, J. Org. Chem., 1993, 58, 3511-3515;
61. D. A. Evans, D. L. Rieger and J. R. Gage, Tetrahedron Lett., 1990, 31, 7099-7100.
62. D. B. Dess and J. C. Martin, J. Org. Chem., 1983, 48, 4155-4156;
63. D. B. Dess and J. C. Martin, J. Am. Chem. Soc., 1991, 113, 7277-7287.
64. M. A. Blanchette, W. Choy, J. T. Davis, A. P. Essenfeld, S. Masamune, W. R. Roush and T. Sakai, Tetrahedron Lett., 1984, 25, 2183-2186.
65. (a) K. B. Sharpless, W. Amberg, Y. L. Bennani, G. A. Crispino, J. Hartung, K.-S. Jeong, H.-L. Kwong, K. Morikawa, Z.-M. Wang, D. Xu and X.-L. Zhang, J. Org. Chem., 1992, 57, 2768-2771;
66. (b) Z. M. Wang and K. B. Sharpless, Tetrahedron Lett., 1993, 34, 8225-8228;
67. (c) H. C. Kolb, M. S. VanNieuwenhze and K. B. Sharpless, Chem. Rev, 1994, 94, 2483-2547.
68. All compounds in this series bearing an acetonide protecting group were found to be sensitive to even mildly acidic conditions, presumably due to the sterically unfavourable 1,2-cis-1,3-trans- nature of the substituents on the 1,3-dioxane ring.
69. N. Nakajima, K. Horita, R. Abe and O. Yonemitsu, Tetrahedron Lett., 1988, 29, 4139-4142.
70. R. E. Ireland, L. Liu and T. D. Roper, Tetrahedron, 1997, 53, 13221-13256.
71. C. Alvarez-Ibarra, S. Arias, G. Banon, M. J. Fernandez, M. Rodriguez and V. Sinisterra, J. Chem. Soc., Chem. Commun., 1987, 1509-1511;
72. I. Paterson, K. S. Yeung and J. B. Smaill, Synlett, 1993, 774-776.
73. N. A. Petasis and E. I. Bzowej, J. Am. Chem. Soc., 1990, 112, 6392-6394.
74. S. V. Ley, J. Norman, W. P. Griffith and S. P. Marsden, Synthesis, 1994, 639-666.
75. K. Griesbaum, A. R. Bandyopadhyay and M. Meister, Can. J. Chem., 1986, 64, 1553-1559.
76. A. J. Mancuso and D. Swern, Synthesis, 1981, 165-185.
77. I. Paterson, K. R. Gibson and R. M. Oballa, Tetrahedron Lett., 1996, 37, 8585-8588;
78. I. Paterson and L. A. Collett, Tetrahedron Lett., 2001, 42, 1187-1191.
79. D. A. Evans, P. J. Coleman and B. Côté, J. Org. Chem., 1997, 62, 788-789;
80. D. A. Evans, B. Cote, P. J. Coleman and B. T. Connell, J. Am. Chem. Soc., 2003, 125, 10893-10898.
81. K. Takai, T. Kakiuchi, Y. Kataoka and K. Utimoto, J. Org. Chem., 1994, 59, 2668-2670.
82. I. Paterson, D. Y.-K. Chen, M. J. Coster, J. L. Acena, J. Bach and D. J. Wallace, Org. Biomol Chem., 2005, 3, DOI: 10.1039/b504151a.