Formal [4 + 2]-Annulation of Chiral Crotylsilanes: Synthesis of the C19-C28 Fragment of Phorboxazoles

Organic Letters

Volumn 3, Issue 11, 2001, Pages 1693-1696

  Huang, Hongbing ^a   Panek, James S ^a  

^a BOSTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

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

ANIMAL; ARTICLE; CATALYSIS; CHEMISTRY; OXIDATION REDUCTION REACTION; SPONGE (PORIFERA); STEREOISOMERISM; SYNTHESIS;

ANIMALS; ANTINEOPLASTIC AGENTS; CATALYSIS; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; INDICATORS AND REAGENTS; OXAZOLES; OXIDATION-REDUCTION; PORIFERA; STEREOISOMERISM;

EID: 0035979063     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015893u     Document Type: Article

References (38)

1. For isolation and biological data see: (a) Searle, P. A.; Molinski, T. T. J. Am. Chem. Soc. 1995, 117, 8126-8131.
2. (b) Searle, P. A.; Molinski, T. T. J. Am. Chem. Soc. 1996, 118, 9422-9423.
3. (c) Molinski, T. F. Tetrahedron Lett. 1996, 37, 7879-7880.
4. Ye, T.; Pattenden, G. Tetrahedron Lett. 1998, 39, 319-322.
5. (b) Pattenden, G.; Plowright, A. T.; Tornos, J. A.; Ye, T. Tetrahedron Lett. 1998, 39, 6099-6102.
6. (c) Paterson, I.; Arnott, E. A. Tetrahedron Lett. 1998, 39, 7185-7188.
7. (d) Williams, D. R.; Clark, M. P.; Berliner, M. A. Tetrahedron Lett. 1999, 40, 2287-2290.
8. (e) Williams, D. R.; Clark, M. P. Tetrahedron Lett. 1999, 40, 2291-2294.
9. (f) Smith, A. B., III; Verhoest, P. R.; Minbiole, K. P.; Lim, J. J. Org. Lett. 1999, 1, 909-912.
10. (g) Smith, A. B., III; Minbiole, K. P.; Verhoest, P. R.; Beauchamp, T. J. Org. Lett. 1999, 1, 913-916.
11. (h) Wolbers, P.; Misske, A. M.; Hoffmann, H. M. R. Tetrahedron Lett. 1999, 40, 4527-4530.
12. (i) Wolbers, P.; Hoffmann, H. M. R. Synthesis 1999, 797-802.
13. (j) Wolbers, P.; Hoffmann, H. M. R. Tetrahedron 1999, 55, 1905-1914.
14. (k) Misske, A. M.; Hoffmann, H. M. R. Tetrahedron 1999, 55, 4315-4324.
15. (l) Rychnovsky, S. D.; Thomas, C. R. Org. Lett. 2000, 2, 1217-1219.
16. (m) Donaldson, W. A.; Greer, P. B. Tetrahedron Lett. 2000, 41, 3801-3803.
17. Forsyth, C. J.; Ahmed, F.; Cink, R. D.; Lee, C. S. J. Am. Chem. Soc. 1998, 120, 5597-5598.
18. (b) Lee, C. S.; Forsyth, C. J. Tetrahedron Lett. 1996, 37, 6449-6452.
19. (c) Cink, R. D.; Forsyth, C. J. J. Org. Chem. 1997, 62, 5672-5673.
20. (d) Ahmed, F.; Forsyth, C. J. Tetrahedron Lett. 1998, 39, 183-186.
21. Evans, D. A.; Cee, V. J.; Smith, T. E.; Fitch, D. M.; Cho, P. S. Angew. Chem., Int. Ed. 2000, 39, 2533-2536.
22. (b) Evans, D. A.; Fitch, D. M. Angew. Chem., Int. Ed. 2000, 39, 2536-2540.
23. (c) Evans, D. A.; Fitch, D. M.; Smith, T. E.; Cee, V. J. J. Am. Chem. Soc. 2000, 122, 10033-10046
24. Huang, H.; Panek, J. S. J. Am. Chem. Soc. 2000, 122, 9836-9837.
25. Schaus, J. V.; Panek, J. S. Org. Lett. 2000, 2, 469-471.
26. We have reported that enantiomerically enriched tetrahydrofurans can be obtained by the reaction of crotylsilanes and aldehydes; see: (a) Panek, J. S.; Yang, M. J. Am. Chem. Soc. 1991, 26, 9868-9870.
27. (b) Beresis, R. T.; Panek, J. S. Bioorg. Med. Chem. Lett. 1993, 13, 1609-1613.
28. (c) For a related tetrahydrofuran synthesis, see: Micalizio, G. C.; Roush, W. R. Org. Lett. 2000, 2, 461-464.
29. Angle, S. R.; El-Said, N. A. J. Am. Chem. Soc. 1999, 121, 10211-10212.
30. The lower diastereoselectivity can be attributed to existence of homoallylic acohol which facilitates the formation of α-epoxide. For a review on substrate-directed reaction, see: Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307-1370.
31. For studies on the mechanism of organocuprate epoxide ring opening, see: (a) Nakamura, E.; Mori, S. Angew. Chem., Int. Ed. 2000, 39, 3750-3771.
32. (b) Mori, S.; Nakamura, E.; Morokuma, K. J. Am. Chem. Soc. 2000, 122, 7294-7307.
33. (a) Furst, A.; Plattner, A. Helv. Chim. Acta 1949, 32, 275-283.
34. (b) Hewbest, H. B.; Smith, M.; Thomas, A. J. Am. Chem. Soc. 1958, 80, 3293-3297.
35. For the similar displacement of primary trifluoromethanesulfonates with the lithium anion of (trimethylsilyl)acetylene, see ref 4
36. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
37. Zhang, H. X.; Guibe, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857-1867.
38. Boden, C. D. J.; Pattenden, G.; Ye, T. J. Chem. Soc., Perkin Trans. 1 1996, 2417-2419.