Total synthesis of swinholide a, preswinholide a, and hemiswinholide a

Chemistry - A European Journal

Volumn 2, Issue 7, 1996, Pages 847-868

  Nicolaou, K C ^a,b   Patron, A P ^a,b   Ajito, K ^a,b   Richter, P K ^a,b   Khatuya, H ^a,b   Bertinato, P ^a,b   Miller, R A ^a,b   Tomaszewski, M J ^a,b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Natural products; Swinholide A; Total syntheses

Indexed keywords

ASYMMETRIC ALKYLATION; COUPLING REACTION; ESTERIFICATION REACTIONS; HYDROXY COMPOUNDS; NATURAL PRODUCTS; RING CLOSURES; SWINHOLIDE A; TOTAL SYNTHESIS;

CARBOXYLIC ACIDS; CHEMICAL BONDS; ESTERIFICATION; ESTERS;

SYNTHESIS (CHEMICAL);

EID: 84891305266     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.19960020718     Document Type: Article

References (92)

1. a) S. Carmely, Y. Kashman, Tetrahedron Lett. 1985, 26, 511;
2. b) C. A. Bewley, N. D. Holland, D. J. Faulkner, Experientia 1996, in press.
3. a) M. Kobayashi, J. Tanaka, T. Katori, M. Matsura, I. Kitagawa, Tetrahedron Lett. 1989, 30, 2963;
4. b) M. Kobayashi, J. Tanaka, T. Katori, M. Matsuura, M. Yamashita, I. Kitagawa, Chem. Pharm. Bull. 1990, 38, 2409;
5. c) I. Kitagawa, M. Kobayashi, T. Katori, M. Yamashita, M. Doi, T. Ishida, J. Tanaka, J. Am. Chem. Soc. 1990, 112, 3710;
6. d) M. Doi, T. Ishida, M. Kobayashi, I. Kitagawa, J. Org. Chem. 1991, 56, 3629.
7. a) M. Kobayashi, J. Tanaka, T. Katori, I. Kitagawa, Chem. Pharm. Bull. 1990, 38, 2960;
8. b) S. Tsukamoto, M. Ishibashi, T. Sasaki, J. Kobayashi, J. Chem. Soc. Perkin Trans 1 1991, 3185.
9. a) Y. Kato, N. Fusetani, S. Matsunaga, K. Hashimoto, R. Sakai, T. Higa, Y. Kashman, Tetrahedron Lett. 1987, 28, 6225;
10. b) J. Tanaka, T. Higa, M. Kobayashi, I. Kitagawa, Chem. Pharm. Bull. 1990, 38, 2967.
11. J. Todd, K. Alvi, P. Crews, Tetrahedron Lett. 1992, 33, 441.
12. a) M. Ishibashi, R. Moore, G. Patterson, C. Xu, J. Clardy, J. Org. Chem 1986, 51, 5300;
13. b) R. Moore, G. Patterson, J. Mynderse, J. Barchi, T. Norton, E. Furusawa, S. Furusawa, Pure Appl. Chem. 1986, 58, 263.
14. a) Y. Shimizu, Chem. Rev. 1993, 93, 1685;
15. b) J. Kobayashi, M. Ishibashi, ibid. 1993, 93, 1753.
16. M. Kobayashi, K. Kawazoe, T. Okamoto, T. Sasaki, I. Kitagawa, Chem. Pharm. Bull. 1994, 42, 19.
17. M. Bubb, I. Spector, A. Bershadsky, E. Korn, J. Biol. Chem. 1995, 270, 3463.
18. a) I. Paterson, J. Cumming, Tetrahedron Lett. 1992, 33, 2847;
19. b) I. Paterson, J. D. Smith, J. Org. Chem. 1992, 57, 3261;
20. c) I. Paterson, K. Yeung, Tetrahedron Lett. 1993, 34, 5347;
21. d) I. Paterson, J. D. Smith, ibid. 1993, 34, 5354;
22. e) I. Paterson, J. G. Cumming, J. D. Smith, R. A. Ward, ibid. 1994, 35, 3405;
23. f) I. Paterson, J. D. Smith, R. A. Ward, J. G. Cumming, J. Am. Chem. Soc. 1994, 116, 2615;
24. g) I. Paterson, J. G. Cumming, R. A. Ward, S. Lamboley, Tetrahedron 1995, 51, 9393;
25. h) I. Paterson, J. D. Smith, R. A. Ward, ibid. 1995, 51, 9413;
26. i) I. Paterson, R. A. Ward, J. D. Smith, J. G. Cumming, K. Yeung, ibid. 1995, 51, 9437.
27. a) T. Nakata, T. Komatsu, K. Nagasawa, Chem. Rev. Bull. 1994, 42, 2403;
28. b) T. Nakata, T. Komatsu, K. Nagasawa, H. Yamada, T. Takahashi, Tetrahedron Lett. 1994, 35, 8225;
29. c) J. Mulzer, F. Meyer, J. Buschmann, P. Luger, ibid. 1995, 36, 3503.
30. a) I. Paterson, K. Yeung, R. A. Ward, J. G. Cumming, J. D. Smith, J. Am. Chem. Soc. 1994, 116, 9391;
31. b) I. Paterson, K. Yeung, R. A. Ward, J. D. Smith, J. G. Cumming, S. Lamboley, Tetrahedron 1995, 51, 9467.
32. a) A. P. Patron, P. K. Richter, M. J. Tomaszewski, R. A. Miller, K. C. Nicolaou, J. Chem. Soc. Chem. Commun. 1994, 1147;
33. b) P. K. Richter, M. J. Tomaszewski, R. A. Miller, A. P. Patron, K. C. Nicolaou, ibid. 1994, 1151.
34. a) E. Boden, G. Keck, J. Org. Chem. 1985, 50, 2394;
35. b) K. C. Nicolaou, S. Seitz, M. Pavia, J. Am. Chem. Soc. 1982, 104, 2030;
36. c) J. Inanaga, K. Hirata, H. Saeki, T. Katsuki, M. Yamaguchi, Bull. Chem. Soc. Jpn. 1979, 52, 1989.
37. a) M. A. Blanchette, W. Choy, J. T. Davis, A. P. Essenfeld, S. Masamune, W. R. Roush, Tetrahedron Lett. 1984, 2183;
38. b) K. C. Nicolaou, S. Seitz, M. Pavia, N. Petasis, J. Org. Chem. 1979, 44, 4011.
39. a) K. C. Nicolaou, J. Daines, W. S. Uenishi, S. P. Papahatjis, T. K. Chakraborty, J. Am. Chem. Soc. 1988, 110, 4672;
40. b) K. C. Nicolaou, T. Chakraborty, R. Daines, N. Simpkins, J. Chem. Soc. Chem. Commun. 1986, 413.
41. a) Y. Gao, K. B. Sharpless, J. Am. Chem. Soc. 1988, 110, 7538;
42. b) B. Kim, K. B. Sharpless, Tetrahedron Lett. 1989, 30, 655;
43. c) B. Lohray, Y. Gao, K. B. Sharpless, ibid. 1989, 30, 2623.
44. a) T. Hoye, K. Crawford, J. Org. Chem. 1994, 59, 520;
45. b) P. A. van der Klein, G. P. H. Boons, G. H. Veeneman, G. A. van der Marel, J. H. van Boom, Tetrahedron Lett. 1989, 30, 5477;
46. c) P. A. M. van der Klein, G. Boons, G. Veeneman, G. A. van der Marel, J. A. van Boom, Synlett 1990, 311.
47. a) T. Mukaiyama, K. Banno, N. Narasaka, J. Am. Chem. Soc. 1974, 96, 7503;
48. b) I. Paterson, L. Price, Tetrahedron Lett. 1981, 22, 2833.
49. a) D. Evans, D. Rieger, M. Bilodeau, F. Urpi, J. Am. Chem. Soc. 1991, 113, 1047;
50. b) D. Evan, M. J. Dart, J. L. Duffy, D. L. Rieger, ibid. 1995, 117, 9073.
51. a) D. Enders, P. Fey, H. Kipphardt, Org. Synth. 1987, 65, 173;
52. b) D. Enders, H. Kipphardt, P. Fey, ibid. 1987, 65, 183;
53. c) D. Enders, H. Eichenauer, Chem. Ber. 1979, 112, 2933;
54. d) D. Enders, H. Eichenauer, Angew. Chem. Int. Ed. Engl. 1979, 18, 397.
55. a) M. Lewis, J. Cha, Y. Kishi, J. Am. Chem. Soc. 1982, 104, 4976;
56. b) Anomeric Effect: Origin and Consequences (Eds.: W. Szarek, D. Horton), ACS Symp. Ser. 1979, 87, ACS, Washington DC;
57. c) K. C. Nicolaou, C.-K. Hwang, M. Duggan, J. Am. Chem. Soc. 1989, 111, 6682.
58. J. Carretero, L. Ghosez, Tetrahedron Lett. 1988, 29, 2059.
59. a) N. Nagashima, M. Ohno, Chem. Lett. Chem. Soc. Jpn. 1987, 141;
60. b) J. Donaldson, S. Grimes, Rev. Silicon, Germanium, Tin, Lead Compd. 1985, 8, 1;
61. c) S. Bunden, P. Cusack, P. Smith, D. Gillies, Inorg. Chim. Acta 1984, 84, 35;
62. d) A. Haines, Adv. Carbohydr. Chem. Biochem. 1976, 33, 11.
63. D. Barton, S. McCombie, J. Chem. Soc. Perkin Trans 1 1975, 1574.
64. a) H. Brown, K. Bhat, J. Am. Chem. Soc. 1986, 108, 293;
65. b) H. Brown, K. Bhat, ibid. 1986, 108, 5919;
66. c) H. Brown, K. Bhat, R. Randad, J. Org. Chem. 1989, 54, 1570;
67. d) W. Roush, K. Ando, D. Powers, A. Palkowitz, R. Halterman, J. Am. Chem. Soc. 1990, 112, 6339.
68. D. Evans, A. Hoveyda, J. Am. Chem. Soc. 1990, 112, 6447.
69. a) S. Rychnovsky, D. Skalitzky, Tetrahedron Lett. 1990, 31, 945;
70. b) D. Evans, D. Rieger, J. Gage, ibid. 1990, 31, 7099.
71. a) H. Brown, K. Bhat, J. Am. Chem. Soc. 1986, 108, 5919;
72. b) H. Brown, K. Bhat, R. Randad, J. Org. Chem. 1989, 54, 1570;
73. c) W. Roush, K. Ando, D. Powers, A. Palkowitz, R. Halterman, J. Am. Chem. Soc. 1990, 112, 6339.
74. a) T. Oishi, T. Nakata, Synthesis 1990, 635;
75. b) G. Cardillo, M. Orena, G. Porzi, S. Sandri, J. Chem. Soc. Chem. Commun. 1981, 465;
76. c) A. Bongini, G. Cardillo, M. Orena, G. Porzi, S. Sandri, J. Org. Chem. 1982, 47, 4626.
77. a) D. A. Evans, S. W. Kaldor, J. Org. Chem. 1990, 55, 1698;
78. b) S. J. Danishefsky, D. M. Armistead, F. E. Wincott, H. G. Selnick, R. Hungate, J. Am. Chem. Soc. 1989, 111, 2967;
79. c) S. J. Danishefsky, S. DeNinno, P. Lartey, ibid. 1987, 109, 2082.
80. a) I. Fleming, T. V. Lee, Tetrahedron Lett, 1981, 705;
81. b) I. Fleming, J. Goldhill, I. Paterson, ibid. 1979, 3205;
82. c) T. Mukaiyama, A. Ishida, Chem. Lett. 1975, 319;
83. d) T. Mukaiyama, A. Ishida, ibid. 1975, 1201.
84. A. J. Mancuso, S. L. Huang, D. Swern, J. Org. Chem. 1978, 43, 2480.
85. V. Kumar, S. Dev, Tetrahedron Lett. 1983, 1289.
86. Modified procedure from: a) E. J. Corey, B. W. Erickson, J. Org. Chem. 1971, 36, 3553;
87. b) E. N. Cain, L. L. Welling, Tetrahedron Lett. 1975, 16, 1356.
88. K. Narasaka, F. C. Pai, Tetrahedron 1984, 40, 2233.
89. S. Kiyooka, H. Kuroda, Y. Shimasaki, Tetrahedron Lett. 1986, 3009.
90. S. H. Graham, D. A. Jonas, J. Chem. Soc. 1969, 188.
91. T. Kappe, F. Fruhwirth, J. Prakt. Chem. 1990, 475.
92. K. C. Nicolaou, K. Ajito, A. P. Patron, H. Khatuya, P. K. Richter, P. Bertinato, J. Am. Chem. Soc. 1996, 118, 3059-3060.