A new enantioselective approach to total synthesis of the Securinega alkaloids: Application to (-)-norsecurinine and phyllanthine

Angewandte Chemie - International Edition

Volumn 39, Issue 1, 2000, Pages 237-240

  Gyoonhee, Han ^a   LaPorte, Matthew G ^a   Folmer, James J ^a   Werner, Kim M ^a   Weinreb, Steven M ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

Alkaloids; Nitrogen heterocycles; Total synthesis

Indexed keywords

ALKALOID DERIVATIVE;

ARTICLE; CYCLIZATION; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; X RAY ANALYSIS;

EID: 0034598513     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000103)39     Document Type: Article

References (44)

1. For reviews see: a) V. Snieckus, The Alkaloids, 1975, 14, 425;
2. b) J. A. Beutler, A. N. Brubaker, Drugs Future 1987, 12, 957.
3. D. Rognan, T. Boulanger, R. Hoffmann, D. P. Vercauteren, J.-M. Andre, F. Durant, C.-G. Wermuth, J. Med. Chem. 1992, 35, 1969.
4. H. Weenen, M. H. H. Nkunya, D. H. Bray, L. B. Mwasumbi, L. S. Kinabo, V. A. Kilimali, J. B. Wijnberg, Planta Med. 1990, 56, 371.
5. J. L. Mensah, I. Lagarde, C. Ceschin, G. Michel, J. Gleye, I. Fouraste, J. Ethnopharmacol. 1990, 28, 129.
6. a) S. Saito, H. Yoshikawa, Y. Sato, H. Nakai, N. Sugimoto, Z. Horii, M. Hanaoka, Y. Tamura, Chem. Pharm. Bull. 1966, 14, 313;
7. b) Z. Horii, T. Imanishi, T. Tanaka, I. Mori, M. Hanaoka, C. Iwata, Chem. Pharm. Bull. 1972, 20, 1768;
8. ) Z. Horii, T. Imanishi, M. Hanaoka, C. Iwata, Chem. Pharm. Bull. 1972, 20, 1774.
9. a) C. H. Heathcock, R. A. Jennings, T. W. von Geldern, J. Org. Chem. 1983, 48, 3428;
10. b) C. H. Heathcock, T. W. von Geldern, Heterocycles 1987, 25, 75.
11. P. A. Jacobi, C. A. Blum, R. W. DeSimone, U. E. S. Udodong, J. Am. Chem. Soc. 1991, 113, 5384.
12. P. Magnus, J. Rodriguez-Lopez, K. Mulholland, I. Matthews, Tetrahedron 1993, 49, 8059.
13. [7] strategies leading to the more common (-)-enantiomer of norsecurinine (5) require D-proline whereas our approach to (-)-5 uses the less-expensive L-amino acid.
14. R. H. Andreatta, V. Nair, A. V. Robertson, W. R. J. Simpson, Aust. J. Chem. 1967, 20, 1493.
15. Compare: G. A. Molander, C. N. Wolfe, J. Org. Chem. 1998, 63, 9031, and references therein. See also: Y. Yamamoto, D. Matsumi, R. Hattori, K. Itoh, J. Org. Chem. 1999, 64, 3224.
16. Compare: G. A. Molander, C. N. Wolfe, J. Org. Chem. 1998, 63, 9031, and references therein. See also: Y. Yamamoto, D. Matsumi, R. Hattori, K. Itoh, J. Org. Chem. 1999, 64, 3224.
17. a) G. Han, M. C. McIntosh, S. M. Weinreb, Tetrahedron Lett. 1994, 35, 5813;
18. b) S. M. Weinreb, J. Heterocycl. Chem. 1996, 33, 1437;
19. c) G. Han, M. G. LaPorte, M. C. McIntosh, S. M. Weinreb, J. Org. Chem. 1996, 61, 9483.
20. a) H. J. Bestmann, D. Sandmeier, Chem. Ber. 1980, 113, 274;
21. b) K. Nickisch, W. Klose, F. Bohlmann, Chem. Ber. 1980, 113, 2038.
22. a) S. Saito, T. Tanaka, K. Kotera, H. Nakai, N. Sugimoto, Z.-I. Horii, M. Ikeda, Y. Tamura, Chem. Pharm. Bull. 1964, 12, 1520;
23. b) S. Saito, T. Tanaka, K. Kotera, H. Nakai, N. Sugimoto, Z.-I. Horii, M. Ikeda, Y. Tamura, Chem. Pharm. Bull. 1965, 13, 786.
24. [14]
25. a) H. J. Reich, S. Wollowitz, Org. React. 1993, 44, 1;
26. b) attempted DDQ or Saegusa oxidations of 23a and 25a also failed;
27. 4 gave significantly lower yields of 5.
28. A similar reaction leading directly to an α-selenophenylenone was described: D. Liotta, C. Barnum, R. Puleo, G. Zima, C. Bayer, H. S. Kezar III, J. Org. Chem. 1981, 46, 2920. See also: K. B. Sharpless, R. F. Lauer, A. Y. Teranishi, J. Am. Chem. Soc. 1973, 95, 6137.
29. A similar reaction leading directly to an α-selenophenylenone was described: D. Liotta, C. Barnum, R. Puleo, G. Zima, C. Bayer, H. S. Kezar III, J. Org. Chem. 1981, 46, 2920. See also: K. B. Sharpless, R. F. Lauer, A. Y. Teranishi, J. Am. Chem. Soc. 1973, 95, 6137.
30. [13] gave only a low yield of butenolide 25b;
31. b) selenides 23b, 25b and 26 are mixtures of epimers at C14.
32. [7]
33. a) P. Muller, D. M. Gilabert, Tetrahedron 1988, 44, 7171;
34. b) J. Larsen, K. A. Jorgensen, J. Chem. Soc. Perkin Trans. 2 1992, 1213.
35. For reviews and lead references to imino Diels-Alder reactions, see: a) D. L. Boger, S. M. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press, Orlando, 1987, ch. 2;
36. b) S. M. Weinreb in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 401.
37. Compare: S. Kobayashi, S. Nagayama, J. Am. Chem. Soc. 1997, 119, 10049.
38. The crystal structure and configuration of cycloadduct 28 were confirmed by X-ray analysis. We thank Dr. M. Shang (University of Notre Dame) for determining this structure.
39. N. Miyoshi, T. Yamamoto, N. Kambe, S. Murai, N. Sonoda, Tetrahedron Lett. 1982, 23, 4813.
40. See also: M. Watanabe, B. Z. Awen, M. Kato, J. Org. Chem. 1993, 58, 3923. This procedure is useful for forming an α-phenylselenoketone from a ketone, although direct formation of an α-phenylselenoenone as occurred with 30 has apparently not previously been observed.
41. This protocol was previously used to dehalogenate an α-bromoenone: A. K. Mandal, S. W. Mahajan, Tetrahedron 1988, 44, 2293.
42. [13] does not give phyllanthine.
43. a) J. Parello, Bull. Soc. Chim. Fr. 1968, 1117;
44. b) D. Arbain, A. A. Birkbeck, L. T. Byrne, M. V. Sargent, B. W. Skelton, A. H. White, J. Chem. Soc. Perkin Trans. 1 1991, 1863.