Total synthesis of the antimicrotubule agent (+)-discodermolide using boron-mediated aldol reactions of chiral ketones

Angewandte Chemie - International Edition

Volumn 39, Issue 2, 2000, Pages 377-380

  Paterson, Ian ^a   Florence, Gordon J ^a   Gerlach, Kai ^a   Scott, Jeremy P ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

Aldol reactions; Antitumor agents; Boron; Natural products; Total synthesis

Indexed keywords

ANTINEOPLASTIC AGENT; BORON; DISCODERMOLIDE; KETONE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0034677179     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000117)39:2<377::AID-ANIE377>3.0.CO;2-E     Document Type: Article

References (48)

1. S. P. Gunasekera, M. Gunasekera, R. E. Longley, G. K. Schulte, J. Org. Chem. 1990, 55, 4912 (Corrigendum: J. Org. Chem. 1991, 56, 1346).
2. S. P. Gunasekera, M. Gunasekera, R. E. Longley, G. K. Schulte, J. Org. Chem. 1990, 55, 4912 (Corrigendum: J. Org. Chem. 1991, 56, 1346).
3. a) E. ter Haar, R. J. Kowalski, E. Hamel, C. M. Lin, R. E. Longley, S. P. Gunasekera, H. S. Rosenkranz, B. W. Day, Biochemistry 1996, 35, 243;
4. b) S. L. Schreiber, J. Chen, D. T. Hung, Chem. Biol. 1996, 3, 287.
5. a) R. J. Kowalski, P. Giannakakou, S. P. Gunasekera, R. E. Longley, B. W. Day, E. Hamel, Mol. Pharmacol. 1997, 52, 613;
6. b) R. Balachandran, E. ter Haar, M. J. Welsh, S. G. Grant, B. W. Day, Anti-Cancer Drugs 1998, 9, 67.
7. a) J. B. Nerenberg, D. T. Hung, P. K. Somers, S. L. Schreiber, J. Am. Chem. Soc. 1993, 115, 12621;
8. b) D.T. Hung, J. B. Nerenberg, S. L. Schreiber, J. Am. Chem. Soc. 1996, 118, 11054;
9. c) A. B. Smith, III, Y. Qui, D. R. Jones, K. Kobayashi, J. Am. Chem. Soc. 1995, 117, 12011;
10. d) S. S. Harried, G. Yang, M. A. Strawn, D. C. Myles, J. Org. Chem. 1997, 62, 6098;
11. e) J. A. Marshall, B. A. Johns, J. Org. Chem. 1998, 63, 7885.
12. a) D. L. Clark, C. H. Heathcock, J. Org. Chem. 1993, 58, 5878;
13. h) I. Paterson, S. P. Wren, J. Chem. Soc. Chem. Commun. 1993, 1790;
14. c) J. M. C. Golec, S. D. Jones, Tetrahedron Lett. 1993, 34, 8159;
15. d) P. L. Evans, J. M. C. Golec, R. J. Gillespie, Tetrahedron Lett. 1993, 34, 8163;
16. e) J. M. C. Golec, R. J. Gillespie, Tetrahedron Lett. 1993, 34, 8167;
17. f) I. Paterson, A. Schlapbach, Synlett 1995, 498;
18. g) M. Miyazawa, S. Oonunia, K. Maruyama, M. Miyashita, Chem. Lett. 1997, 1191;
19. h) M. Miyazawa, S. Oonuma, K. Maruyama, M. Miyashita, Chem. Lett. 1997, 1193;
20. i) J. A. Marshall, Z.-H. Lu, B. A. Johns, J. Org. Chem. 1998, 63, 817;
21. j) D. A. Evans, D. P. Halstead, B. D. Allison, Tetrahedron Lett. 1999, 40, 4461;
22. k) S. A. Filla, J. J. Song, L. Chen, S. Masamune, Tetrahedron Lett. 1999, 40, 5449;
23. A. M. Misske, H. M. R. Hoffmann, Tetrahedron 1999, 55, 4315.
24. a) I. Paterson, M. V. Perkins, Tetrahedron Lett. 1992, 33, 801;
25. h) I. Paterson, J. M. Goodman, M. Isaka, Tetrahedron Lett. 1989, 30, 7121;
26. e) I. Paterson, R. D. Norcross, R. A. Ward, P. Romea, M. A. Lister, J. Am. Chem. Soc. 1994, 116, 11287.
27. J. R. Harrison, A. B. Holmes, I. Collins, Synlett 1999, 972.
28. I. Paterson, E. A. Arnott, Tetrahedron Lett. 1998, 38, 7185.
29. D. A. Evans, A. Hoveyda, J. Am. Chem. Soc. 1990, 112, 6447.
30. a) M. Petrzilka, Helv. Chem. Acta 1978, 61, 3075;
31. b) J. W. Burton, J. S. Clark, S. Derrer, T. C. Stork, J. G. Bendall, A. B. Holmes, J. Am. Chem. Soc. 1997, 119, 7483.
32. a) B. Neises, W. Steglich, Angew. Chem. 1978, 90, 556; Angew. Chem. Int. Ed. Engl. 1978, 17, 522;
33. a) B. Neises, W. Steglich, Angew. Chem. 1978, 90, 556; Angew. Chem. Int. Ed. Engl. 1978, 17, 522;
34. b) G. Hölfe, W. Steglich, H. Vorbrüggen, Angew. Chem. 1978, 90, 602; Angew. Chem. Int. Ed. Engl. 1978, 17, 569.
35. b) G. Hölfe, W. Steglich, H. Vorbrüggen, Angew. Chem. 1978, 90, 602; Angew. Chem. Int. Ed. Engl. 1978, 17, 569.
36. I. Paterson, D. J. Wallace, C. J. Cowden, Synthesis 1998, 639.
37. It was crucial to lower the temperature to - 100 C in order to suppress partial decomposition of the lithium enolate. a) S. H. Montgomery, M. C. Pirrung, C. H. Heathcock, Org. Synth. Coll. Vol. 1990, 7, 190; b) M. C. Pirrung, C. H. Heathcock, J. Org. Chem. 1980, 45, 1727; c) I. Paterson, Tetrahedron Lett. 1983, 24, 1311.
38. It was crucial to lower the temperature to - 100 C in order to suppress partial decomposition of the lithium enolate. a) S. H. Montgomery, M. C. Pirrung, C. H. Heathcock, Org. Synth. Coll. Vol. 1990, 7, 190; b) M. C. Pirrung, C. H. Heathcock, J. Org. Chem. 1980, 45, 1727; c) I. Paterson, Tetrahedron Lett. 1983, 24, 1311.
39. It was crucial to lower the temperature to - 100 C in order to suppress partial decomposition of the lithium enolate. a) S. H. Montgomery, M. C. Pirrung, C. H. Heathcock, Org. Synth. Coll. Vol. 1990, 7, 190; b) M. C. Pirrung, C. H. Heathcock, J. Org. Chem. 1980, 45, 1727; c) I. Paterson, Tetrahedron Lett. 1983, 24, 1311.
40. A. De Mico, R. Margarita, L. Parlanti, A. Vescovi, G. Piancatelli, J. Org. Chem. 1997, 62, 6974.
41. W. C. Still, C. Gennari, Tetrahedron Lett. 1983, 24, 4405.
42. P. Kocovsky, Tetrahedron Lett. 1986, 27, 5521.
43. I. Paterson, G. J. Florence, unpublished results.
44. a) I. Paterson, J. M. Goodman, M. A. Lister, R. C. Schumann, C. K. McClure, R. D. Norcross. Tetrahedron 1990, 46, 4663;
45. b) I. Paterson, R. M. Oballa, R. D. Norcross, Tetrahedron Lett. 1996, 37, 8581.
46. For a review of asymmetric aldol reactions using boron enolates, see C. J. Cowden, I. Paterson, Org. React. 1997, 51, 1.
47. a) D. A. Evans, K. T. Chapman, E. M. Carreira, J. Am. Chem. Soc. 1988, 110, 3560;
48. b) A. K. Saksena, P. Mangiaracina, Tetrahedron Lett. 1983, 24, 273.