Synthesis of the C31-C67 fragment of amphidinol 3

Angewandte Chemie - International Edition

Volumn 45, Issue 43, 2006, Pages 7258-7262

  De Vicente, Javier ^a   Huckins, John R ^a   Rychnovsky, Scott D ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Julia olefination; Natural products; Polyenes; Polyketides; Tetrahydropyran

Indexed keywords

OLEFINS; ORGANIC POLYMERS; SYNTHESIS (CHEMICAL);

JULIA OLEFINATION; NATURAL PRODUCTS; POLYENES; POLYKETIDES; TETRAHYDROPYRAN;

ALCOHOLS;

ALKENE; AMPHIDINOL 3; PYRAN DERIVATIVE;

ARTICLE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS;

ALKENES; MOLECULAR CONFORMATION; PYRANS; STEREOISOMERISM;

EID: 33750972054     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200602742     Document Type: Article

References (46)

1. a) G. K. Paul, N. Matsumori, M. Murata, K. Tachibana, Tetrahedron Lett. 1995, 36, 6279;
2. b) M. Satake, M. Murata, T. Yasumoto, T. Fujita, H. Naoki, J. Am. Chem. Soc. 1991, 113, 9859;
3. c) T. Houdai, S. Matsuoka, M. Murata, M. Satake, S. Ota, Y. Oshima, L. L. Rhodes, Tetrahedron 2001, 57, 5551;
4. d) M. Murata, S. Matsuoka, N. Matsumori, G. K. Paul, K. Tachibana, J. Am. Chem. Soc. 1999, 121, 870;
5. e) G. K. Paul, N. Matsumori, K. Konoki, M. Murata, K. Tachibana, J. Mar. Biotech. 1997, 5, 124;
6. f) G. K. Paul, N. Matsumori, K. Konoki, M. Sasaki, M. Murata, K. Tachibana in Harmful and Toxic Algal Blooms. Proceedings of Seventh International Conference on Toxic Phytoplankton (Eds.: T. Yasumoto, Y. Oshima, Y. Fukuyo), UNESCO, Sendai, Japan, 1996, p. 503.
7. N. Matsumori, D. Kaneno, M. Murata, H. Nakamura, K. Tachibana, J. Org. Chem. 1999, 64, 866.
8. a) J. de Vicente, B. Betzemeier, S. D. Rychnovsky, Org. Lett. 2005, 7, 1853;
9. b) S. BouzBouz, J. Cossy, Org. Lett. 2001, 3, 1451;
10. c) E. M. Flamme, W. R. Roush, Org. Lett. 2005, 7, 1411;
11. d) J. D. Hicks, E. M. Flamme, W. R. Roush, Org. Lett. 2005, 7, 5509;
12. e) L. A. Paquette, S.-K. Chang, Org. Lett. 2005, 7, 3111;
13. f) S.-K. Chang, L. A. Paquette, Synlett 2005, 2915;
14. g) C. Dubost, I. E. Marko, J. Bryans, Tetrahedron Lett. 2005, 46, 4005.
15. a) L. Ayala, C. G. Lucero, J. A. C. Romero, S. A. Tobacco, K. A. Woerpel, J. Am. Chem. Soc. 2003, 125, 15 521;
16. b) R. V. Stevens, A. W. M. Lee, J. Am. Chem. Soc. 1979, 101, 7032;
17. c) R. V. Stevens, Acc. Chem. Res. 1984, 17, 289;
18. d) P. Deslongchamps, Stereoelectronic Effects in Organic Chemistry, Pergamon, New York, 1983, pp. 209-221.
19. J.-M. Brunel, P. Diter, M. Deutsch, H. B. Kagan, J. Org. Chem. 1995, 60, 8086.
20. B. M. Trost, S. Mallart, Tetrahedron Lett. 1993, 34, 8025.
21. The major isomer of 7 was purified by MPLC before the Mosher analysis: a) M. J. Rieser, Y. H. Hui, J. K. Rupprecht, J. F. Kozlowski, K. V. Wood, J. L. McLaughlin, P. R. Hanson, Z. Zhuang, T. R. Hoye, J. Am. Chem. Soc. 1992, 114, 10 203;
22. b) J. A. Dale, H. S. Mosher, J. Am. Chem. Soc. 1973, 95, 512;
23. c) G. R. Sullivan, J. A. Dale, H. S. Mosher, J. Org. Chem. 1973, 38, 2143;
24. d) I. Ohtani, T. Kusumi, Y. Kashman, H. Kakisawa, J. Am. Chem. Soc. 1991, 113, 4092.
25. a) A. Basha, M. Lipton, S. M. Weinreb, Tetrahedron Lett. 1977, 18, 4171;
26. b) J. I. Levin, E. Turos, S. M. Weinreb, Synth. Commun. 1982, 12, 989.
27. D. L. Comins, A. Dehghani, Tetrahedron Lett. 1992, 33, 6299.
28. W. J. Scott, J. K. Stille, J. Am. Chem. Soc. 1986, 108, 3033.
29. R. Pappo, D. S. Allen, Jr., R. U. Lemieux, W. S. Johnson, J. Org. Chem. 1956, 21, 478.
30. D. B. Dess, J. C. Martin, J. Org. Chem. 1983, 48, 4155.
31. a) K. Sonagashira, Y. Todah, N. Hagihara, Tetrahedron Lett. 1975, 16, 4467;
32. b) M. Alami, F. Ferri, G. Linstrumelle, Tetrahedron Lett. 1993, 34, 6403.
33. a) H. C. Brown, S. K. Gupta, J. Am. Chem. Soc. 1972, 94, 4370;
34. b) H. C. Brown, T. Hamaoka, N. Ravindran, J. Am. Chem. Soc. 1973, 95, 5786.
35. a) E.-I. Negishi, Acc. Chem. Res. 1982, 15, 340;
36. b) E.-I. Negishi, T. Takahashi, S. Baba, D. E. Van Horn, N. Okukado, J. Am. Chem. Soc. 1987, 109, 2393.
37. a) S. L. Huang, K. Omura, D. Swern, J. Org. Chem. 1976, 41, 3329;
38. b) T. T. Tidwell, Org. React. 1990, 39, 297.
39. Y. Wang, F. G. West, Synthesis 2002, 99.
40. LiDBB is a reducing agent for arene radical anions, first reported by Freeman et al.: P. K. Freeman, L. L. Hutchinson, J. Org. Chem. 1980, 45, 1924.
41. O. Mitsunobu, Synthesis 1981, 1.
42. H. S. Schultz, H. B. Freyermuth, S. R. Buc, J. Org. Chem. 1963, 28, 1140.
43. J. R. Parikh, W. v. E. Doering, J. Am. Chem. Soc. 1967, 89, 5505.
44. a) P. R. Blakemore, W. J. Cole, P. J. Kocienski, A. Morley, Synlett 1998, 26;
45. b) P. R. Blakemore, J. Chem. Soc. Perkin Trans. 1 2002, 2563.
46. M. Julia, J. M. Paris, Tetrahedron Lett. 1973, 14, 4833.