Synthesis of the diazonamide A macrocyclic core via a Dieckmann-Type cyclization

Organic Letters

Volumn 3, Issue 16, 2001, Pages 2451-2454

  Vedejs, Edwin ^a   Zajac, Matthew A ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; DIAZONAMIDE A; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FUSED HETEROCYCLIC RINGS; MARINE TOXIN; OXAZOLE DERIVATIVE;

ARTICLE; CHEMISTRY; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

ANTINEOPLASTIC AGENTS; CYCLIZATION; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MARINE TOXINS; OXAZOLES;

EID: 0035833678     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016097r     Document Type: Article

References (37)

1. Lindquist, N.; Fenical, W.; Van Duyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 2303-2304.
2. Konopelski, J. P.; Hottenroth, J. M.; Oltra, H. M.; Veliz, E. A.; Yang, Z. C. Synlett 1996, 609.
3. (a) Vedejs, E.; Wang, J. Abstracts of Papers, 212th National Meeting of the American Chemical Society, Boston, August 1996; American Chemical Society: Washington, DC, 1996; ORGN 93.
4. (b) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031.
5. (c) Vedejs, E.; Barda, D. A. Org. Lett. 2000, 2, 1033.
6. (a) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997, 2413.
7. (b) Bagley, M. C.; Moody, C. J.; Pepper, A. G. Tetrahedron Lett. 2000, 41, 6901.
8. (a) Wipf, P.; Yokokawa, F. Tetrahedron Lett. 1998, 39, 2223.
9. (b) Wipf, P.; Methot, J. Org. Lett. 2001, 3, 1261.
10. Boto, A.; Ling, M.; Meek, G.; Pattenden, G. Tetrahedron Lett. 1998, 39, 8167.
11. Chan, F.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 835.
12. Nicolaou, K. C.; Snyder, S. A.; Simonsen, K. B.; Koumbis, A. E. Angew. Chem., Int. Ed. 2000, 39, 3473.
13. (a) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640.
14. (b) Chen, X.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2000, 39, 937.
15. Fuerst, D. E.; Stoltz, B. M.; Wood, J. L. Org. Lett. 2000, 2, 3521.
16. (a) Lach, F.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6893.
17. (b) Bagley, M. C.; Hind, S. L.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6897.
18. (a) Magnus, P.; Kreisberg, J. D. Tetrahedron Lett. 1999, 40, 451.
19. (b) Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 831.
20. (c) Kreisberg, J. D.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2001, 42, 627.
21. Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem. 1994, 66, 2107.
22. Hang, H. C.; Drotleff, E.; Elliott, G. I.; Ritsema, T. A.; Konopelski, J. P. Synthesis 1999, 398.
23. (a) Stoll, M. Chimia 1948, 2, 217.
24. (b) Leonard, N. J.; Schimelpfenig, C. W. J. Org. Chem. 1958, 23, 1708.
25. (c) Tse, B. J. Am. Chem. Soc. 1996, 118, 7094.
26. Vedejs, E.; Monahan, S. D. J. Org. Chem. 1996, 61, 5192.
27. Schröder, R.; Schöllkopf, U.; Blume, E.; Hoppe, I. Liebigs Ann. Chem. 1975, 533
28. Adam, W.; Peters, K.; Sauter, M. Synthesis 1994, 111.
29. Black, T. H.; Arrivo, S. M.; Schumm, J. S.; Knobeloch, J. M. J. Org. Chem. 1987, 52, 5425.
30. Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508.
31. For macrocyclization at -23 °C, ΔG* = 15.5 kcal/mol corresponds to a half-life of ca. 5 s for atropisomer interconversion.
32. 4a
33. Oldroyd, D. L.; Weedon, A. C. J. Org. Chem. 1994, 59, 1333. Morales-Rios, M. S.; Joseph-Nathan, P. Magn. Reson. Chem. 1987, 25, 911.
34. Oldroyd, D. L.; Weedon, A. C. J. Org. Chem. 1994, 59, 1333. Morales-Rios, M. S.; Joseph-Nathan, P. Magn. Reson. Chem. 1987, 25, 911.
35. In a preliminary study, intermediate 21 has also been made from benzofuran as shown below: (equation presented)
36. For leading references to oxazole side chain lithiation, see: Lipshutz, B. H.; Hungate, R. W. J. Org. Chem. 1981, 46, 1410. Evans, D. A.; Cee, V. J.; Smith, T. E.; Santiago, K. J. Org. Lett. 1999, 1, 87.
37. For leading references to oxazole side chain lithiation, see: Lipshutz, B. H.; Hungate, R. W. J. Org. Chem. 1981, 46, 1410. Evans, D. A.; Cee, V. J.; Smith, T. E.; Santiago, K. J. Org. Lett. 1999, 1, 87.