Diastereo- and enantioselective total synthesis of stigmatellin A

Chemistry - A European Journal

Volumn 6, Issue 8, 2000, Pages 1302-1309

  Enders, Dieter ^a   Geibel, Gunter ^a   Osborne, Simon ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Aldol reactions; Asymmetric synthesis; Hydrazones; Natural products; Total synthesis

Indexed keywords

ANTIBIOTIC AGENT; HYDRAZONE DERIVATIVE; POLYENE; STIGMATELLIN;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHEMISTRY; DIASTEREOISOMER; ENANTIOMER; REACTION ANALYSIS; REDUCTION; SPECTROSCOPY; STEREOISOMERISM; STRUCTURE ANALYSIS; SYNTHESIS;

ANTIBIOTICS; MOLECULAR STRUCTURE; POLYENES; SPECTRUM ANALYSIS; STEREOISOMERISM; SUPPORT, NON-U.S. GOV'T;

EID: 0034647038     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3765(20000417)6:8<1302::aid-chem1302>3.0.co;2-j     Document Type: Article

References (55)

1. a) G. Höfle, B. Kunze, C. Zorin, H. Reichenbach, Liebigs Ann. 1984, 1883
2. b) B. Kunze, G. Höfle, H. Reichenbach, J. Antibiotics 1987, 40, 258
3. c) B. Kunze, T. Kemmer, G. Höfle, H. Reichenbach, J. Antibiotics 1984, 37, 454.
4. T. D. Brock, M. T. Madigan, Biology of Microorganisms, 6th ed., Prentice-Hall Englewood Cliffs, New Jersey, 1991.
5. R. Dillert, Dissertation, Braunschweig, 1989.
6. a) G. von Jagow, T. Ohnishi, FEBS Lett. 1985, 185, 2592
7. b) M. Strohdeicher, B. Neuß, S. Bringer-Meyer, H. Sahm, Arch. Microbiol. 1990, 154, 536
8. c) R. M. Bourne, P. R. Rich, Biochem. Soc. Trans. 1991, 19, 251
9. d) J. Fernandez-Valesco, A. R. Crofts, Biochem. Soc. Trans. 1991, 19, 588
10. e) U. Brandt, U. Haase, H. Schägger, G. von Jagow, J. Biol. Chem. 1991, 266, 19958
11. f) R. E. Cleland, D. S. Bendall, Photosyn. Res. 1992, 34, 409
12. g) U. Liebl, S. Pezennec, A. Riedel, E. Kellner, W. Nitschke, J. Biol. Chem. 1992, 267, 14068
13. h) M. K. Tokito, F. Daldal, Mol. Microbiol. 1993, 9, 965
14. i) D. Esposti, A. Ghelli, M. Crimi, E. Estornell, R. Fato, G. Lenaz, Biochem. Biophys. Res. Commun. 1993, 190, 1090.
15. G. Thierbach, B. Kunze, H. Reichenbach, G. Höfle, Biochim. Biophys. Acta 1984, 765, 227.
16. W. Oettmeier, D. Godde, B. Kunze, G. Höfle, Biochim. Biophys. Acta 1985, 807, 216.
17. T. Ohnishi, U. Brandt, G. von Jagow. Eur. J. Biochem. 1988, 176, 385.
18. D. Enders, S. Osborne, J. Chem. Soc. Chem. Commun. 1993, 424.
19. a) D. Enders in Asymmetric Synthesis, Vol. 3 (Ed.: J. D. Morrison), Academic Press, Orlando, 1984, p. 275
20. b) D. Enders, Chem. Scripta 1985, 65, 139
21. c) D. Enders, P. Fey, H. Kipphardt, Org. Synth. 1987, 65, 173, 183.
22. a) D. A. Evans, J. S. Clark, R. Metternich, V.J. Novack, G.S. Sheppard, J. Am. Chem. Soc. 1990, 112, 866
23. b) D. A. Evans, F. Urpi, T. C. Somers, J. S. Clark, M. T. Bilodeau, J. Am. Chem. Soc. 1990, 112, 8215
24. c) D. A. Evans, D. L. Rieger, M. T. Bilodeau, F. Urpi, J. Am. Chem. Soc. 1991, 113, 1047.
25. N. N. Schwartz, J. H. Blumbergs, J. Org. Chem. 1964, 29, 1976.
26. For some recent alkylations see; a) P. Kündig, R. Liu, A. Ripa, Helv. Chim. Acta 1992, 75, 2657 b) D. Enders, U. Jegelka, Tetrahedron Lett. 1993, 34, 2453 c) D. Enders, J. Tiebes, N. De Kimpe, M. Keppens, C. Stevens, G. Smagghe, O. Betz, J. Org. Chem. 1993, 58, 4881 d) D. Enders, A. Plant, K. Drechsel, O. F. Prokopenko, Liebigs Ann. 1995, 1127.
27. For some recent alkylations see; a) P. Kündig, R. Liu, A. Ripa, Helv. Chim. Acta 1992, 75, 2657 b) D. Enders, U. Jegelka, Tetrahedron Lett. 1993, 34, 2453 c) D. Enders, J. Tiebes, N. De Kimpe, M. Keppens, C. Stevens, G. Smagghe, O. Betz, J. Org. Chem. 1993, 58, 4881 d) D. Enders, A. Plant, K. Drechsel, O. F. Prokopenko, Liebigs Ann. 1995, 1127.
28. For some recent alkylations see; a) P. Kündig, R. Liu, A. Ripa, Helv. Chim. Acta 1992, 75, 2657 b) D. Enders, U. Jegelka, Tetrahedron Lett. 1993, 34, 2453 c) D. Enders, J. Tiebes, N. De Kimpe, M. Keppens, C. Stevens, G. Smagghe, O. Betz, J. Org. Chem. 1993, 58, 4881 d) D. Enders, A. Plant, K. Drechsel, O. F. Prokopenko, Liebigs Ann. 1995, 1127.
29. For some recent alkylations see; a) P. Kündig, R. Liu, A. Ripa, Helv. Chim. Acta 1992, 75, 2657 b) D. Enders, U. Jegelka, Tetrahedron Lett. 1993, 34, 2453 c) D. Enders, J. Tiebes, N. De Kimpe, M. Keppens, C. Stevens, G. Smagghe, O. Betz, J. Org. Chem. 1993, 58, 4881 d) D. Enders, A. Plant, K. Drechsel, O. F. Prokopenko, Liebigs Ann. 1995, 1127.
30. M. S. Manhas, W. H. Hoffmann, B. Lei, A. K. Bose, J. Chem. Soc. Perkin Trans. 1 1975, 461.
31. J. C. Heslin, C. J. Moody, J. Chem. Soc. Perkin Trans. 1 1988, 1417.
32. a) D. Enders, A. Plant. Synlett 1990, 725
33. b) D. Enders, A. Plant, Synlett 1994, 1032
34. c) R. Fernandez, C. Gasch, J.-M. Lassaletta, J.-M. Liera, J. Vasquez, Tetrahedron 1993, 34, 141
35. d) D. Enders, A. Plant, D. Backhaus, U. Reinhold. Tetrahedron 1995, 51, 10699.
36. a) A. Fairbourne, G. P. Gibson, D.W. Stephens, J. Am. Chem. Soc. 1931, 53, 456
37. b) H. C. Arndt, S. A. Carroll, Synthesis 1979, 202
38. c) Y. Vo-Quang, M. Daumas, L. Vo-Quang, F. LeGoffic, Synthesis 1989, 64.
39. D. A. Evans, K. T. Chapman, E. M. Carreira, J. Am. Chem. Soc. 1988, 110, 3560.
40. G. R. Scarlato, J. A. DeMattei, L. S. Chong, A. K. Ogawa, M. R. Lin, R. W. Armstrong, J. Org. Chem. 1996, 61, 6139.
41. R. Johansson, B. Samuelsson, J. Chem. Soc. Perkin Trans. 1 1984, 2371.
42. a) E. J. Corey, G. Schmidt, Tetrahedron Lett. 1979, 20, 399
43. b) E. J. Corey, G. Schmidt, Tetrahedron Lett. 1980, 21, 731.
44. T. Schmidlin, W. Zürcher, C. Tamm. Helv. Chim. Acta 1981, 64, 235.
45. E. J. Corey, D. E. Cane, L. Libit, J. Am. Chem. Soc. 1971, 93, 7016.
46. a) A. K. Bhattacharya, G. Thyagarajan, Chem. Rev, 1981, 81, 415
47. b) L. Lombardo, R. J. K. Taylor, Synthesis 1978, 131.
48. a) G. P. Ellis, Chromenes, Chromanones and Chramones, Wiley, New York, 1977
49. b) C. Crivelli, S. von Kostanecki, Chem. Ber. 1900, 33, 2512
50. c) W. Baker, J. Chem. Soc. 1933, 1381
51. d) K. Venkataraman, J. Chem. Soc. 1934, 1767
52. e) J. Staunton, D. H. R. Barton, W. D. Ollis, Comprehensive Organic Chemistry, Vol. 4, Pergamon, London 1979, p. 659
53. f) A. Ueno, K. Hirakawa, S. Fukushima, T. Noro, K. Morinaga, Chem. Pharm. Bull. 1978, 26, 2407.
54. I. Hirao, M. Yamaguchi, M. Hamada, Synthesis 1984, 1076.
55. K. C. Nicolaou, R. A. Daines, T. K. Chakraborty, Y. Ogawa, J. Am. Chem. Soc. 1988, 110, 4685.