Total Synthesis of (-)-Apicularen A

Journal of the American Chemical Society

Volumn 126, Issue 8, 2004, Pages 2425-2430

  Su, Qibin ^a   Panek, James S ^a  

^a BOSTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ESTERIFICATION; ESTERS; SODIUM COMPOUNDS;

ANNULATION; ASYMMETRIC SYNTHESIS;

SYNTHESIS (CHEMICAL);

APICULAREN A; NATURAL PRODUCT; NITRILE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOSELECTIVITY; LACTONIZATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; TRANSESTERIFICATION;

ALLYL COMPOUNDS; ANTINEOPLASTIC AGENTS; BICYCLO COMPOUNDS, HETEROCYCLIC; MACROLIDES; MYXOCOCCALES; SILANES; STEREOISOMERISM;

EID: 1542366700     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja037957x     Document Type: Article

References (42)

1. Kunze, B.; Jansen, R.; Sasse, F.; Höfle, G.; Reichenbach, H. J. Antibiot. 1998, 51, 1075.
2. Jansen, R.; Kunze, B.; Reichenbach, H.; Höfle, G. Eur. J. Org. Chem. 2000, 913.
3. Kwon, J. H.; Kim, D. H.; Shim, J. S.; Ahn, J. W. J. Microbiol. Biotechnol. 2002, 12, 702.
4. For previous total syntheses of apicularen A, see: (a) Bhattacharjee, A. ; Seguil, O. R.; De Brabander, J. K. Tetrahedron Lett. 2001, 42, 1217.
5. (b) Nicolaou, K. C.; Kim, D. W.; Baati, R. Angew. Chem., Int. Ed. 2002, 41, 3701.
6. For studies toward syntheses of apicularen A, see: (c) Bhattacharjee, A. ; De Brabander, J. K. Tetrahedron Lett. 2000, 41, 8069.
7. (d) Lewis, A.; Stefanuti, I.; Swain, S. A.; Smith, S. A.; Taylor, R. J. K. Tetrahedron Lett. 2001, 42, 5549.
8. (e) Kuhnert, S. M.; Maier, M. E. Org. Lett. 2002, 4, 643.
9. (f) Lewis, A.; Stefanuti, I.; Swain, S. A.; Smith, S. A.; Taylor, R. J. K. Org. Biomol. Chem. 2003, 1, 104.
10. (g) Graetz, B. R.; Rychnovsky, S. D. Org. Lett. 2003, 5, 3357.
11. For preparation of amide side chain, 3, see: (a) Labrecque, D.; Charron, S.; Rej, R.; Blais, C.; Lamothe, S. Tetrahedron Lett. 2001, 42, 2645.
12. (b) Fürstner, A.; Dierske, T.; Thiel, O.; Blanda, G. Chem.-Eur. J. 2001, 7, 5286.
13. (c) Snider, B. B.; Song, F. Org. Lett. 2000, 2, 407.
14. Jadhav, P. K.; Bhat, K. S.; Perumal, P. T.; Brown, H. C. J. Org. Chem. 1986, 51, 432.
15. For related annulations, see: (a) Huang, H.; Panek, J. S. J. Am. Chem. Soc. 2000, 122, 9836.
16. (b) Huang, H.; Panek, J. S. Org. Lett. 2003, 5, 1991.
17. (c) Roush, W. R.; Dilley, G. J. Synlett 2001, S1, 955.
18. Lambert, J. B. Tetrahedron 1990, 46, 2677.
19. Ayala, L.; Lucero, C. G.; Romero, J. A. C.; Tabacco, S. A.; Woerpel, K. A. J. Am. Chem. Soc. 2003, 125, 15521 and references therein.
20. Chauret, D. C.; Chong, J. M.; Ye, Q. Tetrahedron: Asymmetry 1999, 10, 3601.
21. Beresis, R. T.; Solomon, J. S.; Yang, M.; Jain, N. F.; Panek, J. S. Org. Synth. 1997, 75, 78.
22. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
23. Peterson, D. J. J. Org. Chem. 1968, 33, 780.
24. Brown, H. C.; Geoghegan, P., Jr. J. Am. Chem. Soc. 1967, 89, 1522.
25. Brown, H. C.; Zweifel, G. J. Am. Chem. Soc. 1959, 81, 247.
26. Huang, H.; Panek, J. S. Org. Lett. 2001, 3, 1693.
27. Hayakawa, H.; Iida, K.; Miyazawa, M.; Miyashita, M. Chem. Lett. 1999, 601.
28. (a) Saiah, M.; Bessodes, M.; Antonakis, K. Tetrahedron Lett. 1992, 33, 4317.
29. (b) Mitsunobu, O. Synthesis 1981, 1.
30. Niwa, H.; Hida, T.; Yamada, K. Tetrahedron Lett. 1981, 22, 4239.
31. Iversen, T.; Bundle, K. R. J. Chem. Soc., Chem. Commun. 1981, 1240.
32. Corey, E. J.; Suggs, J. W. Tetrahedron Lett. 1975, 31, 2647.
33. Maercker, A. Org. React. 1965, 14, 270.
34. Jadhav, P. K.; Bhat, K. S.; Perumal, P. T.; Brown, H. C. J. Org. Chem. 1986, 51, 432.
35. For base-induced intermolecular transesterification reaction of cyanomethyl ester, see: (a) Scherlock, M. H. S. African Pat. ZA 6802187, CAN 70, 106224.
36. (b) Shen, R.; Lin, C. T.; Porco, J. A., Jr. J. Am. Chem. Soc. 2002, 124, 5650.
37. Hugel, H. M.; Bhaskar, K. V.; Longmore, R. W. Synth. Commun. 1992, 22, 693.
38. For selectively protecting phenol, see: Kelly, T. R.; Jagoe, C. T.; Li, Q. J. Am. Chem. Soc. 1989, 111, 4522.
39. Takai, K.; Nitta, K.; Utimoto, K. J. Am. Chem. Soc. 1986, 108, 7408. For an optimization of the solvent system for Takai olefination reaction, see: Evans, D. A.; Black, W. C. J. Am. Chem. Soc. 1993, 115, 4497.
40. Takai, K.; Nitta, K.; Utimoto, K. J. Am. Chem. Soc. 1986, 108, 7408. For an optimization of the solvent system for Takai olefination reaction, see: Evans, D. A.; Black, W. C. J. Am. Chem. Soc. 1993, 115, 4497.
41. (a) Shen, R.; Porco, J. A., Jr. Org. Lett. 2000, 2, 1333.
42. (b) Shen, R.; Lin, C.; Bowman, E.; Bowman, B. J.; Porco, J. A., Jr. J. Am. Chem. Soc. 2003, 125, 7889.